Hydrazine-Substituted Anthranilic Acid Derivatives

ABSTRACT

The present invention constitutes new hydrazine-substituted anthranilic acid derivatives of the general formula (I), 
     
       
         
         
             
             
         
       
     
     in which R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , Qx, A, Qy and n have the definitions indicated in the description, application thereof as insecticides and acaricides for controlling animal pests, alone and in combination with further agents for activity boosting, and a number of processes for their preparation.

The present invention relates to new hydrazine-substituted anthranilicacid derivatives, to their application as insecticides and acaricidesfor controlling animal pests, alone and in combination with furtheragents for activity boosting, and to a number of processes for theirpreparation.

Anthranilic acid derivatives having insecticidal properties have alreadybeen described in the literature, as for example in WO 01/70671, WO03/015519, WO 03/016284, WO 03/015518, WO 03/024222, WO 03/016282, WO03/016283, WO 03/062226, WO 03/027099, WO 04/027042, WO 04/033468, WO2004/046129, WO 2004/067528, WO 2005/118552, WO 2005/077934, WO2005/085234, WO 2006/023783, WO 2006/000336, WO 2006/040113, WO2006/111341, WO 2007/006670, WO 2007/024833, WO2007/020877, WO2007/144100, WO2007/043677, WO2008/126889, WO2008/126890, WO2008/126933.

In their application, however, the active ingredients already known inaccordance with the specifications identified above have disadvantagesin some respects, whether it be that they exhibit a narrow spectrum ofapplication or whether it be that they do not have satisfactoryinsecticidal or acaricidal activity.

New hydrazine-substituted anthranilic acid derivatives have now beenfound which have advantages over the compounds already known, examplesbeing better biological or environmental properties, broader applicationmethods, an improved insecticidal or acaricidal activity, and also highcompatibility with crop plants. The hydrazine-substituted anthranilicacid derivatives can be used in combination with further agents forenhancing the activity, particularly against insects which are difficultto control.

The present invention accordingly provides new hydrazine-substitutedanthranilic acid derivatives of the formula (I)

in which

R¹ is hydrogen, amino or hydroxyl or is C₁-C₆-alkyl, C₂-C₆-alkenyl,C₂-C₆-alkynyl or C₃-C₆-cycloalkyl, each of which is optionallysubstituted one or more times by identical or different substituents,the substituents being selectable independently of one another fromhalogen, cyano, nitro, hydroxyl, C₁-C₄-alkoxy, C₁-C₄-alkylthio,C₁-C₄-alkylsulphinyl, C₁-C₄-alkylsulphonyl, (C₁-C₄-alkoxy)carbonyl,C₁-C₄-alkylamino, di(C₁-C₄-alkyl)amino, C₃-C₆-cycloalkylamino or(C₁-C₄-alkyl)C₃-C₆-cycloalkylamino,

R², R³ independently of one another are hydrogen, C₂-C₆-alkoxycarbonyl,C₂-C₆-alkylcarbonyl, C₂-C₆-alkylaminocarbonyl,C₂-C₆-dialkylaminocarbonyl or are C₁-C₆-alkyl, C₁-C₆-alkoxy,C₂-C₆-alkenyl, C₂-C₆-alkynyl or C₃-C₆-cycloalkyl, each of which isoptionally substituted one or more times by identical or differentsubstituents, the substituents being selectable independently of oneanother from halogen, cyano, nitro, hydroxyl, C₁-C₆-alkyl,C₃-C₆-cycloalkyl, C₁-C₄-alkoxy, C₁-C₄-haloalkoxy, C₁-C₄-alkylthio,C₁-C₄-alkylsulphinyl, C₁-C₄-alkylsulphonyl, C₁-C₄-alkylsulphimino,C₁-C₄-alkylsulphimino-C₁-C₄-alkyl,C₁-C₄-alkylsulphimino-C₂-C₅-alkylcarbonyl, C₁-C₄-alkylsulphoximino,C₁-C₄-alkylsulphoximino-C₁-C₄-alkyl,C₁-C₄-alkylsulphoximino-C₂-C₅-alkylcarbonyl, C₂-C₆-alkoxycarbonyl,C₂-C₆-alkylcarbonyl or C₃-C₆-trialkylsilyl, or

R², R³ independently of one another are a phenyl ring or a 5- or6-membered unsaturated, partially saturated or saturated heterocycle,the phenyl ring or heterocycle being optionally substituted one or moretimes by identical or different substituents, and the substituents beingselectable independently of one another from hydrogen, C₁-C₆-alkyl,C₂-C₆-alkenyl, C₂-C₆-alkynyl, C₃-C₆-cycloalkyl, C₁-C₆-haloalkyl,C₂-C₆-haloalkenyl, C₂-C₆-haloalkynyl, C₃-C₆-halocycloalkyl, halogen, CN,(C═O)OH, (C═O)NH₂, NO₂, OH, C₁-C₄-alkoxy, C₁-C₄-haloalkoxy,C₁-C₄-alkylthio, C₁-C₄-alkylsulphinyl, C₁-C₄-alkylsulphonyl,C₁-C₄-haloalkylthio, C₁-C₄-haloalkylsulphinyl, C₁-C₄-haloalkylsulphonyl,C₁-C₄-alkylamino, di(C₁-C₄-alkyl)amino, C₃-C₆-cycloalkylamino,(C₁-C₆-alkyl)carbonyl, (C₁-C₆-alkoxy)carbonyl,(C₁-C₆-alkyl)aminocarbonyl, di(C₁-C₄-alkyl)aminocarbonyl,tri(C₁-C₂)alkylsilyl, (C₁-C₄-alkyl)(C₁-C₄-alkoxy)imino, or

R² and R³ may be joined to one another via two to six carbon atoms andform a ring which optionally additionally contains a further nitrogen,sulphur or oxygen atom and may optionally be substituted one to fourtimes by C₁-C₂-alkyl, C₁-C₂-haloalkyl, halogen, cyano, amino,C₁-C₂-alkoxy or C₁-C₂-haloalkoxy,

R⁴ is a group selected from —C(═S)—R⁸, —C(═)—R⁸, —C(═O)—OR⁹, —C(═S)—OR⁹,—C(═O)—SR¹⁰, —C(═S)—SR¹⁰, —C(═O)—NR¹¹R¹², —C(═S)—NR¹¹R¹², —S(O)₂—R¹³ and—S(O)₂—NR¹⁴R¹⁵

or R³ and R⁴ together are ═CR¹⁶ if R² and R³ are not joined to oneanother via two to six carbon atoms and do not form a ring,

R⁵ is hydrogen, halogen, cyano, nitro, C₁-C₄-alkyl, C₁-C₄-haloalkyl,C₂-C₆-alkenyl, C₂-C₆-haloalkenyl, C₂-C₆-alkynyl, C₁-C₄-alkoxy,C₁-C₄-haloalkoxy, SF₅, C₁-C₄-alkylthio, C₁-C₄-alkylsulphinyl,C₁-C₄-alkylsulphonyl, C₁-C₄-haloalkylthio, C₁-C₄-haloalkylsulphinyl,C₁-C₄-haloalkylsulphonyl, C₁-C₄-alkylamino, di(C₁-C₄-alkyl)amino,C₃-C₆-cycloalkylamino, (C₁-C₄-alkoxy)imino,(C₁-C₄-alkyl)(C₁-C₄-alkoxy)imino, (C₁-C₄-haloalkyl)(C₁-C₄-alkoxy)iminoor C₃-C₆-trialkylsilyl, or

two radicals R⁵ form, via adjacent carbon atoms, a ring which is—(CH₂)₃—, —(CH₂)₄—, —(CH₂)₅—, —(CH═CH—)₂—, —OCH₂O—, —O(CH₂)₂O—, —OCF₂O—,—(CF₂)₂O—, —O(CF₂)₂O—, —(CH═CH—CH═N)— or —(CH═CH—N═CH)—, or

two radicals R⁵, furthermore, form via adjacent carbon atoms the fusedrings below, which are optionally substituted one or more times byidentical or different substituents, the substituents being selectableindependently of one another from hydrogen, cyano, C₁-C₆-alkyl,C₃-C₆-cycloalkyl, C₁-C₆-haloalkyl, C₃-C₆-halocycloalkyl, halogen,C₁-C₆-alkoxy, C₁-C₄-alkylthio-(C₁-C₆-alkyl),C₁-C₄-alkylsulphinyl(C₁-C₆-alkyl), C₁-C₄-alkylsulphonyl(C₁-C₆-alkyl),C₁-C₄-alkylamino, di(C₁-C₄-alkyl)amino or C₃-C₆-cycloalkylamino,

n is 0 to 3,

X is O or S,

R⁶ is C₁-C₆-alkyl, C₃-C₆-cycloalkyl, C₁-C₆-haloalkyl,C₁-C₆-halocycloalkyl, C₂-C₆-alkenyl, C₂-C₆-haloalkenyl, C₂-C₆-alkynyl,C₂-C₆-haloalkynyl, C₁-C₄-alkoxy, C₁-C₄-haloalkoxy, C₁-C₄-alkylthio,C₁-C₄-alkylsulphinyl, C₁-C₄-alkylsulphonyl, C₁-C₄-haloalkylthio,C₁-C₄-haloalkyl-sulphinyl, C₁-C₄-haloalkylsulphonyl, halogen, cyano,nitro or C₃-C₆-trialkylsilyl,

Q_(X) is an aromatic or heteroaromatic 5- to 6-membered ring which isoptionally substituted one or more times by identical or differentsubstituents R⁷ and which may contain 1-3 heteroatoms from the series N,S and O,

A is optionally singly or multiply substituted —(C₁-C₆-alkylene)-,—(C₁-C₆-alkenylene)-, —(C₁-C₆-alkynylene)-,—R¹⁷—(C₃-C₆-cycloalkyl)-R¹⁷—, —R¹⁷—O—R¹⁷—, —R¹⁷—S—R¹⁷—, —R¹⁷—S(═O)—R¹⁷—,—R¹⁷—S(═O)₂—R¹⁷—, —R¹⁷—NH—(C₁-C₆-alkyl)-, —R¹⁷—N(C₁-C₆-alkyl)-R¹⁷,—R¹⁷—C═NO(C_(1-C) ₆-alkyl), —CH[CO₂(C₁-C₆-alkyl)-, —R¹⁷—C(═O)—R¹⁷,—R¹⁷—C(═O)NH—R¹⁷, R¹⁷—C(═O )N(C₁-C₆-alkyl)-R¹⁷, —R¹⁷—C(═O)NHNH—R¹⁷—,—R¹⁷—C(═O)N(C₁-C₆-alkyl)-NH—R¹⁷—, —R¹⁷—C(═O)NHN(C₁-C₆-alkyl)-R¹⁷,—R¹⁷—O(C═O)—R¹⁷, —R¹⁷—O(C═O)NH—R¹⁷, —R¹⁷—O(C═O)N(C₁-C₆-alkyl)-R¹⁷,—R¹⁷—S(═O)₂NH—R¹⁷, —R¹⁷—S(═O)₂N(C₁-C₆-alkyl)-R¹⁷, —R¹⁷—S(C═O)—R¹⁷,—R¹⁷—S(C═O)NH—R¹⁷, —R¹⁷—S(C═O)N(C₁-C₆-alkyl)-R¹⁷, —R¹⁷—NHNH—R¹⁷,—R¹⁷—NHN(C₁-C₆-alkyl)-R¹⁷, —R¹⁷—N(C₁-C₆-alkyl)-NH—R¹⁷,—R¹⁷—N(C₁-C₆-alkyl)-N(C₁-C₆-alkyl)-R¹⁷, —R¹⁷—N═CH—O—R¹⁷,—R¹⁷—NH(C═O)O—R¹⁷, —R¹⁷—N(C₁-C₆-alkyl)-(C═O)O—R¹⁷, —R¹⁷—NH(C═O)NH—R¹⁷,—R¹⁷—NH(C═S)NH—R¹⁷, —R¹⁷—NHS(═O)₂—R¹⁷ or —R¹⁷—N(C₁-C₆-alkyl)S(═O)₂—R¹⁷,

the substituents being selectable independently of one another fromhalogen, cyano, nitro, hydroxyl, C₁-C₆-alkyl, C₁-C₆-alkoxy andhalo-C₁-C₆-alkyl,

where —(C₃-C₆-cycloalkyl)- in the ring may optionally contain 1 to 2heteroatoms selected from the series N, S and O,

R¹⁷ is linear or branched —(C₁-C₆-alkylene)- or is a direct bond,

and two or more radicals R¹⁷ independently of one another are linear orbranched —(C₁-C₆-alkylene)- or are a direct bond,

for example, R¹⁷—O—R¹⁷— is —(C₁-C₆-alkylene)-O—C₁-C₆-alkylene)-,—(C₁-C₆-alklene)-O—, —O—(C₁-C₆-alkylene)-, or —O—,

Q_(Y) is a 5- or 6-membered, partially saturated or saturatedheterocyclic or heteroaromatic ring or an aromatic 8-, 9- or 10-memberedfused heterobicyclic ring system or is phenyl, the ring or ring systembeing optionally substituted one or more times by identical or differentsubstituents, and the substituents being selectable independently of oneanother from hydrogen, C₁-C₆-alkyl, C₂-C₆-alkenyl, C₂-C₆-alkynyl,C₃-C₆-cycloalkyl, C₁-C₆-haloalkyl, C₂-C₆-haloalkenyl, C₂-C₆-haloalkynyl,C₃-C₆-halocycloalkyl, halogen, CN, CO₂H, CO₂NH₂, NO₂, OH, C₁-C₄-alkoxy,C₁-C₄-haloalkoxy, C₁-C₄-alkylthio, C₁-C₄-alkylsulphinyl,C₁-C₄-alkylsulphonyl, C₁-C₄-haloalkylthio, C₁-C₄-haloalkylsulphinyl,C₁-C₄-haloalkylsulphonyl, C₁-C₄-alkylamino, di(C ₁-C₄-alkyl)amino,C₃-C₆-cycloalkylamino, (C₁-C₆-alkyl)carbonyl, (C₁-C₆-alkoxy)carbonyl,(C₁-C₆-alkyl)aminocarbonyl, di(C₁-C₄-alkyl)aminocarbonyl,tri(C₁-C₂)alkylsilyl and (C₁-C₄-alkyl)(C₁-C₄-alkoxy)imino,

or the substituents being selectable independently of one another fromphenyl or a 5- or 6-membered heteroaromatic ring, where phenyl or thering may optionally be substituted one or more times by identical ordifferent C₁-C₆-alkyl, C₂-C₆-alkenyl, C₂-C₆-alkynyl, C₃-C₆-cycloalkyl,C₁-C₆-haloalkyl, C₂-C₆-haloalkenyl, C₂-C₆-haloalkynyl,C₃-C₆-halocycloalkyl, halogen, CN, NO₂, OH, C₁-C₄-alkoxy andC₁-C₄-haloalkoxy substituents,

R⁷ is hydrogen, C₁-C₆-alkyl, C₂-C₆-alkenyl, C₂-C₆-alkynyl,C₃-C₆-cycloalkyl, C₁-C₆-haloalkyl, C₂-C₆-haloalkenyl, C₃-C₆-cycloalkoxyor

R independently at each occurrence is hydrogen, C₁-C₆-alkyl,C₃-C₆-cycloalkyl, C₁-C₆-haloalkyl, halogen, cyano, nitro, C₁-C₄-alkoxy,C₁-C₄-haloalkoxy, C₁-C₄-alkylthio, C₁-C₄-haloalkylthio,C₁-C₄-haloalkylsulphonyl or (C₁-C₄-alkyl)C₁-C₄-alkoxyimino,

m is 0 to 4,

Z is N, CH, CF, CCl, CBr or CI,

R⁸ is hydrogen or is C₁-C₆-alkyl, C₂-C₆-alkenyl, C₂-C₆-alkynyl,C₃-C₁₂-cycloalkyl, C₃-C₁₂-cycloalkyl-C₁-C₆-alkyl or C₄-C₁₂-bicycloalkyl,each of which is optionally substituted one or more times by identicalor different substituents, the substituents being selectableindependently of one another from halogen, cyano, nitro, hydroxyl,C₁-C₆-alkyl, C₃-C₆-cycloalkyl, C₁-C₄-alkoxy, C₁-C₄-haloalkoxy,C₁-C₄-alkylthio, C₁-C₄-alkylsulphinyl, C₁-C₄-alkylsulphonyl,C₁-C₄-alkylsulphimino, C₁-C₄-alkylsulphimino-C₁-C₄-alkyl,C₁-C₄-alkylsulphimino-C₂-C₅-alkylcarbonyl, C₁-C₄-alkylsulphoximino,C₁-C₄-alkylsulphoximino-C₁-C₄-alkyl,C₁-C₄-alkylsulphoximino-C₂-C₅-alkylcarbonyl, C₂-C₆-alkoxycarbonyl,C₂-C₆-alkylcarbonyl, C₃-C₆-trialkylsilyl, amino, C₁-C₄-alkylamino,di(C₁-C₄-alkyl)amino, C₃-C₆-cycloalkylamino, a phenyl ring or a 3- to6-membered unsaturated, partially saturated or saturated heterocycle,the phenyl ring or heterocycle being optionally substituted one or moretimes by identical or different substituents, and the substituents beingselectable independently of one another from hydrogen, C₁-C₆-alkyl,C₂-C₆-alkenyl, C₂-C₆-alkynyl, C₃-C₆-cycloalkyl, C₁-C₆-haloalkyl,C₂-C₆-haloalkenyl, C₂-C₆-haloalkynyl, C₃-C₆-halocycloalkyl, halogen, CN,(C═O)OH, CONH₂, NO₂, OH, C₁-C₄-alkoxy, C₁-C₄-haloalkoxy,C₁-C₄-alkylthio, C₁-C₄-alkylsulphinyl, C₁-C₄-alkylsulphonyl,C₁-C₄-haloalkylthio, C₁-C₄-haloalkylsulphinyl, C₁-C₄-haloalkylsulphonyl,C₁-C₄-alkylamino, di(C₁-C₄-alkyl)amino, C₃-C₆-cycloalkylamino,(C₁-C₆-alkyl)carbonyl, (C₁-C₆-alkoxy)carbonyl,(C₁-C₆-alkyl)aminocarbonyl, di(C₁-C₄-alkyl)aminocarbonyl,tri(C₁-C₂)alkylsilyl or (C₁-C₄-alkyl)(C₁-C₄-alkoxy)imino,

R⁸ additionally is a phenyl ring or a 3- to 6-membered unsaturated,partially saturated or saturated heterocycle, the heteroatoms beingselected from the series N, S and O, where the phenyl ring orheterocycle is optionally substituted one or more times by identical ordifferent substituents, and where the substituents are selectableindependently of one another from hydrogen, C₁-C₆-alkyl, C₂-C₆-alkenyl,C₂-C₆-alkynyl, C₃-C₆-cycloalkyl, C₁-C₆-haloalkyl, C₂-C₆-haloalkenyl,C₂-C₆-haloalkynyl, C₃-C₆-halocycloalkyl, halogen, CN, (C═O)OH, CONH₂,NO₂, OH, C₁-C₄-alkoxy, C₁-C₄-haloalkoxy, C₁-C₄-alkylthio,C₁-C₄-alkylsulphinyl, C₁-C₄-alkylsulphonyl, C₁-C₄-haloalkylthio,C₁-C₄-haloalkylsulphinyl, C₁-C₄-haloalkylsulphonyl, C₁-C₄-alkylamino,di(C₁-C₄-alkyl)amino, C₃-C₆-cycloalkylamino, (C₁-C₆-alkyl)carbonyl,(C₁-C₆-alkoxy)carbonyl, (C₁-C₆-alkyl)aminocarbonyl,di(C₁-C₄-alkyl)aminocarbonyl, tri(C₁-C₂)alkylsilyl or(C₁-C₄-alkyl)(C₁-C₄-alkoxy)imino,

R⁹, R¹⁰, R¹³, R¹⁴ and R¹⁵ independently of one another are C₁-C₆-alkyl,C₂-C₆-alkenyl, C₂-C₆-alkynyl, C₃-C₁₂-cycloalkyl,C₃-C₁₂-cycloalkyl-C₁-C₆-alkyl or C₄-C₁₂-bicycloalkyl, each of which isoptionally substituted one or more times by identical or differentsubstituents, the substituents being selectable independently of oneanother from halogen, cyano, nitro, hydroxyl, C₁-C₆-alkyl,C₃-C₆-cycloalkyl, C₁-C₄-alkoxy, C₁-C₄-haloalkoxy, C₁-C₄-alkylthio,C₁-C₄-alkylsulphinyl, C₁-C₄-alkylsulphonyl, C₁-C₄-alkylsulphimino,C₁-C₄-alkylsulphimino-C₁-C₄-alkyl,C₁-C₄-alkylsulphimino-C₂-C₅-alkylcarbonyl, C₁-C₄-alkylsulphoximino,C₁-C₄-alkylsulphoximino-C₁-C₄-alkyl,C₁-C₄-alkylsulphoximino-C₂-C₅-alkylcarbonyl, C₂-C₆-alkoxycarbonyl,C₂-C₆-alkylcarbonyl, C₃-C₆-trialkylsilyl, amino, C₁-C₄-alkylamino,di(C₁-C₄-alkyl)amino, C₃-C₆-cycloalkylamino, a phenyl ring or a 3- or6-membered unsaturated, partially saturated or saturated heterocycle,the phenyl ring or heterocycle being optionally substituted one or moretimes by identical or different substituents, and the substituents beingselectable independently of one another from hydrogen, C₁-C₆-alkyl,C₂-C₆-alkenyl, C₂-C₆-alkynyl, C₃-C₆-cycloalkyl, C₁-C₆-haloalkyl,C₂-C₆-haloalkenyl, C₂-C₆-haloalkynyl, C₃-C₆-halocycloalkyl, halogen, CN,(C═O)OH, CONH₂, NO₂, OH, C₁-C₄-alkoxy, C₁-C₄-haloalkoxy,C₁-C₄-alkylthio, C₁-C₄-alkylsulphinyl, C₁-C₄-alkylsulphonyl,C₁-C₄-haloalkylthio, C₁-C₄-haloalkylsulphinyl, C₁-C₄-haloalkylsulphonyl,C₁-C₄-alkylamino, di(C₁-C₄-alkyl)amino, C₃-C₆-cycloalkylamino,(C₁-C₆-alkyl)carbonyl, (C₁-C₆-alkoxy)carbonyl,(C₁-C₆-alkyl)aminocarbonyl, di(C₁-C₄-alkyl)aminocarbonyl,tri(C₁-C₂)alkylsilyl or (C₁-C₄-alkyl)(C₁-C₄-alkoxy)imino,

R⁹, R¹⁰, R¹³, R¹⁴ and R¹⁵ independently of one another are additionallya phenyl ring or are a 3- to 6-membered unsaturated, partially saturatedor saturated heterocycle, the heteroatoms being selected from the seriesN, S and O, the phenyl ring or heterocycle being optionally substitutedone or more times by identical or different substituents, and thesubstituents being selectable independently of one another fromhydrogen, C₁-C₆-alkyl, C₂-C₆-alkenyl, C₂-C₆-alkynyl, C₃-C₆-cycloalkyl,C₁-C₆-haloalkyl, C₂-C₆-haloalkenyl, C₂-C₆-haloalkynyl,C₃-C₆-halocycloalkyl, halogen, CN, (C═O)OH, CONH₂, NO₂, OH,C₁-C₄-alkoxy, C₁-C₄-haloalkoxy, C₁-C₄-alkylthio, C₁-C₄-alkylsulphinyl,C₁-C₄-alkylsulphonyl, C₁-C₄-haloalkylthio, C₁-C₄-haloalkylsulphinyl,C₁-C₄-haloalkylsulphonyl, C₁-C₄-alkylamino, di(C₁-C₄-alkyl)amino,C₃-C₆-cycloalkylamino, (C₁-C₆-alkyl)carbonyl, (C₁-C₆-alkoxy)carbonyl,(C₁-C₆-alkyl)aminocarbonyl, di(C₁-C₄-alkyl)aminocarbonyl,tri(C₁-C₂)alkylsilyl or (C₁-C₄-alkyl)(C₁-C₄-alkoxy)imino,

R¹¹, R¹² independently of one another are hydrogen or are R⁹,

R¹⁶ is a phenyl ring or is a 5- or 6-membered heteroaromatic ring, theheteroatoms being selected from the series N, S and O, the ring beingoptionally substituted one or more times by identical or differentsubstituents, and the substituents being selectable independently of oneanother from hydrogen, C₁-C₆-alkyl, C₂-C₆-alkenyl, C₂-C₆-alkynyl,C₃-C₆-cycloalkyl, C₁-C₆-haloalkyl, C₂-C₆-haloalkenyl, C₂-C₆-haloalkynyl,C₃-C₆-halocycloalkyl, halogen, CN, (C═O)OH, CONH₂, NO₂, OH,C₁-C₄-alkoxy, C₁-C₄-haloalkoxy, C₁-C₄-alkylthio, C₁-C₄-alkylsulphinyl,C₁-C₄-alkylsulphonyl, C₁-C₄-haloalkylthio, C₁-C₄-haloalkylsulphinyl,C₁-C₄-haloalkylsulphonyl, C₁-C₄-alkylamino, di(C₁-C₄-alkyl)amino,C₃-C₆-cycloalkylamino, (C₁-C₆-alkyl)carbonyl, (C₁-C₆-alkoxy)carbonyl,(C₁-C₆-alkyl)aminocarbonyl, di(C₁-C₄-alkyl)aminocarbonyl,tri(C₁-C₂)alkylsilyl or (C₁-C₄-alkyl)(C₁-C₄-alkoxy)imino, the compoundsof the general formula (I) further comprise N-oxides and salts.

The compounds of the formula (I) may possibly be present in differentpolymorphic forms or as a mixture of different polymorphic forms. Boththe pure polymorphs and the polymorph mixtures are provided by theinvention and can be used in accordance with the invention.

The compounds of the formula (I) optionally include diastereomers orenantiomers.

A general definition of the compounds of the invention is provided bythe formula (I). Preferred, more preferred and very preferred arecompounds of the formula (I) in which

R¹ preferably is hydrogen, C₁-C₆-alkyl, C₂-C₆-alkenyl, C₂-C₆-alkynyl,C₃-C₆-cycloalkyl, cyano(C₁-C₆-alkyl), C₁-C₆-haloalkyl,C₂-C₆-haloalkenyl, C₂-C₆-haloalkynyl, C₁-C₄-alkoxy-C₁-C₄-alkyl,C₁-C₄-alkylthio-C₁-C₄-alkyl, C₁-C₄-alkylsulphinyl-C₁-C₄-alkyl orC₁-C₄-alkyl-sulphonyl-C₁-C₄-alkyl,

R¹ more preferably is hydrogen, methyl, ethyl, cyclopropyl, cyanomethyl,methoxymethyl, methylthiomethyl, methylsulphinylmethyl ormethylsulphonylmethyl,

R¹ very preferably is hydrogen,

R² and R³ independently of one another preferably are hydrogen or areC₁-C₆-alkyl or C₃-C₆-cycloalkyl optionally substituted one or more timesby identical or different substituents, the substituents beingselectable independently of one another from halogen, cyano,C₂-C₆-alkoxycarbonyl or C₂-C₆-alkylcarbonyl,

R², R³ independently of one another more preferably are hydrogen,methyl, ethyl, isopropyl, tert-butyl,

R⁴ preferably is —C(═)—R⁸, —C(═O)—OR⁹, —C(═O)—SR¹⁰, —C(═O)—NR¹¹R¹²,—S(O)₂—R¹³, —S(O)₂—NR¹⁴R^(15,)

R⁴ more preferably is —C(═)—R⁸ or —C(═O)—OR⁹,

R⁵ preferably is hydrogen, C₁-C₄-alkyl, C₁-C₄-haloalkyl, halogen, cyano,C₁-C₄-alkoxy, C₁-C₄-haloalkoxy, C₁-C₄-alkylthio or C₁-C₄-haloalkylthio,

two adjacent radicals R⁵ likewise preferably are —(CH₂)₃—, —(CH₂)₄—,—(CH₂)₅—, —(CH═CH—)₂—, —OCH₂O—, —O(CH₂)₂O—, —OCF₂O—, —(CF₂)₂O—,—O(CF₂)₂O—, —(CH═CH—CH═N)— or —(CH═CH—N═CH)—,

R⁵ more preferably is hydrogen, C₁-C₄-alkyl, C₁-C₂-haloalkyl, halogen,cyano or C₁-C₂-haloalkoxy,

two adjacent radicals R⁵ more preferably are —(CH₂)₄—, —(CH═CH—)₂—,—O(CH₂)₂O—, —O(CF₂)₂O—, —(CH═CH—CH═N)— or —(CH═CH—N═CH)—,

R⁵ very preferably is hydrogen, methyl, trifluoromethyl, cyano, fluoro,chloro, bromo, iodo or trifluoromethoxy,

two adjacent radicals R⁵ very preferably are —(CH₂)₄—, or —(CH═CH—)₂—,

R⁵ more particularly preferably is chlor, fluoro or bromo,

R⁵ additionally more particularly preferably is iodo or cyano,

two adjacent radicals R⁵ more particularly preferably are —(CH═CH—)₂,

n preferably is 0 to 2,

n more preferably is 1 or 2,

n very preferably is 2,

X preferably is O or S,

X more preferably and very preferably is O,

R⁶ preferably is C₁-C₄-alkyl, C₃-C₆-cycloalkyl, C₁-C₄-haloalkyl,C₁-C₆-halocycloalkyl, C₂-C₆-alkenyl, C₂-C₄-haloalkenyl, C₂-C₄-alkynyl,C₂-C₄-haloalkynyl, C₁-C₄-alkoxy, C₁-C₄-haloalkoxy, C₁-C₄-alkylthio,C₁-C₄-alkylsulphinyl, C₁-C₄-alkylsulphonyl, C₁-C₄-haloalkylthio,C₁-C₄-haloalkylsulphinyl, C₁-C₄-haloalkylsulphonyl, halogen, cyano,nitro or C₃-C₆-trialkylsilyl,

R⁶ more preferably is C₁-C₄-alkyl, C₃-C₆-cycloalkyl, C₁-C₄-haloalkyl,C₁-C₆-halocycloalkyl, C₂-C₆-alkenyl, C₂-C₄-haloalkenyl, C₂-C₄-alkynyl,C₂-C₄-haloalkynyl, C₁-C₄-alkoxy, C₁-C₄-haloalkoxy, fluoro, chloro,bromo, iodo, cyano, nitro or C₃-C₆-trialkylsilyl,

R⁶ very preferably is methyl, fluoro, chloro, bromo or iodo,

R⁶ more particularly preferably is methyl or chloro,

Q_(X) preferably is a heteroaromatic 5-membered ring which is optionallysubstituted one or more times by identical or different substituents R⁷and which may contain 1-3 heteroatoms from the series N, O and S, is aheteroaromatic 6-membered ring which is optionally substituted one ormore times by identical or different substituents R⁷ and which maycontain 1-3 nitrogen atoms, or is phenyl,

Q_(X) more preferably is a 5- or 6-membered ring which is optionallysubstituted one or more times by identical or different substituents R⁷and is selected from the group consisting of furan, thiophene, pyrazole,triazole, imidazole, thiazole, oxazole, isoxazole, isothiazole,thiadiazole, oxadiazole, pyrrole, pyridine, pyrimidine, pyridazine andpyrazine,

Q_(X) very preferably is pyrazole, thiazole or pyrimidine which issubstituted singly by the group

where Z, R and m may have the stated general definitions or thepreferred or more preferred definitions,

A preferably is optionally singly or multiply substituted—(C₁-C₄-alkylene)-, —(C₁-C₄-alkenylene)-, —(C₁-C₄-alkynylene)-,—R¹⁷—(C₃-C₆-cycloalkyl)-R¹⁷—, —R¹⁷—O—R¹⁷—, —R¹⁷—S—R¹⁷—, —R¹⁷—S(═O)—R¹⁷—,—R¹⁷—S(═O)₂—R¹⁷—, —R¹⁷—NH—(C₁-C₄-alkyl)-, —R¹⁷—N(C₁-C₄-alkyl)-R¹⁷,—R¹⁷—C═NO(C₁-C₄-alkyl), —R¹⁷—C(═O)—R¹⁷, —R¹⁷—C(═S)—R¹⁷,—R¹⁷—C(═O)NH—R¹⁷, R¹⁷—C(═O)N(C₁-C₄-alkyl)-R¹⁷, —R¹⁷—S(═O)₂NH—R¹⁷,—R¹⁷—S(═O)₂N(C₁-C₄-alkyl)-R¹⁷, —R¹⁷—NH(C═O)O—R¹⁷,—R¹⁷—N(C₁-C₄-alkyl)-(C═O)O—R¹⁷, —R¹⁷—NH(C═O)NH—R¹⁷, —R¹⁷—NHS(═O)₂—R¹⁷ or—R¹⁷—N(C₁-C₄-alkyl)S(═O)₂—R¹⁷, the substituents being selectableindependently of one another from halogen, cyano, nitro, hydroxyl,C₁-C₆-alkyl, C₁-C₆-alkoxy or halo-C₁-C₆-alkyl,

A more preferably is —CH₂—, —CH₂O—, —CH₂OCH₂—, —CH₂S—, —CH₂SCH₂—,—CH₂N(C₁-C₄-alkyl)-, —CH₂N(C₁-C₄-alkyl)CH₂—, —CH(Hal)-, —C(Hal)₂-,—CH(CN)—, CH₂(CO)—, CH₂(CS)—, CH₂CH(OH)—, -cyclopropyl-, CH₂(CO)CH₂—,—CH(C₁-C₄-alkyl)-, —C(di-C₁-C₆-alkyl)-, —CH₂CH₂—, —CH═CH—, —C≡C— or—C═NO(C₁-C₆-alkyl),

A very preferably is —CH₂—, —CH(CH₃), C(CH₃)₂, —CH₂CH₂—, —CH(CN)— or—CH₂O—,

A more particularly preferably is CH₂, CH(CH₃) or —CH₂O—,

R⁷ preferably is C₁-C₆-alkyl or is the radical

R⁷ additionally preferably is C₃-C₆-cycloalkoxy,

R⁷ more preferably is methyl or is the radical

R independently at each occurrence preferably is hydrogen, halogen,cyano, C₁-C₄-alkyl, C₁-C₄-alkoxy, C₁-C₄-haloalkyl, C₁-C₄-haloalkoxy,C₁-C₄-haloalkylsulphonyl or (C₁-C₄-alkoxyimino,

R independently at each occurrence more preferably is hydrogen, halogen,cyano or C₁-C₄-haloalkyl,

R independently at each occurrence very preferably is fluoro, chloro orbromo,

R more particularly preferably is chloro,

m preferably is 1, 2 or 3,

m more preferably is 1 or 2,

m very preferably is 1,

Z preferably is N, CH, CF, CCl, CBr or CI,

Z more preferably is N, CH, CF, CCl or CBr,

Z very preferably is N, CCl or CH,

R⁸ preferably is hydrogen or singly or multiply identically ordifferently substituted C₁-C₆-alkyl or C₃-C₆-cycloalkyl, thesubstituents being selectable independently of one another from halogen,cyano, a phenyl ring or a 3- or 6-membered unsaturated, partiallysaturated or saturated heterocycle, the phenyl ring or heterocycle beingoptionally substituted one or more times by identical or differentsubstituents, and the substituents being selectable independently of oneanother from hydrogen, C₁-C₆-alkyl, C₁-C₆-haloalkyl, halogen, cyano,NO₂, C₁-C₄-alkoxy or C₁-C₄-haloalkoxy,

R⁸ additionally preferably is a phenyl ring or is a 3- to 6-memberedunsaturated, partially saturated or saturated heterocycle, theheteroatoms being selected from the series N, S and O, and the phenylring or heterocycle being optionally substituted one or more times byidentical or different substituents, and the substituents beingselectable independently of one another from hydrogen, C₁-C₆-alkyl,C₁-C₆-haloalkyl, halogen or cyano,

R⁸ more preferably is hydrogen, is methyl, ethyl, isopropyl ortert-butyl optionally singly or multiply identically or differentlysubstituted, the substituents being selectable independently of oneanother from halogen, cyano, phenyl or pyridyl, where phenyl or pyridylis optionally substituted one or more times by identical or differenthydrogen, trifluoromethyl, cyano, fluoro, chloro, bromo ortrifluoromethoxy substituents,

R⁸ additionally more preferably is phenyl, pyridyl or is a 3- to6-membered saturated heterocycle, containing 1-2 heteroatoms from theseries N, S and O, the phenyl or pyridyl ring or heterocycle beingoptionally substituted one or more times by identical or differentsubstituents, and the substituents being selectable independently of oneanother from hydrogen, C₁-C₆-alkyl, C₁-C₆-haloalkyl, halogen or cyano,

R⁹, R¹⁰, R¹³, R¹⁴ and R¹⁵ independently of one another preferably aresingly or multiply identically or differently substituted C₁-C₆-alkyl orC₃-C₆-cycloalkyl, the substituents being selectable independently of oneanother from halogen, cyano, a phenyl ring or a 3- to 6-memberedunsaturated, partially saturated or saturated heterocycle, the phenylring or heterocycle being optionally substituted one or more times byidentical or different substituents, and the substituents beingselectable independently of one another from hydrogen, C₁-C₆-alkyl,C₁-C₆-haloalkyl, halogen, cyano, NO₂, C₁-C₄-alkoxy or C₁-C₄-haloalkoxy,

R⁹, R¹⁰, R¹³, R¹⁴, R¹⁵ independently of one another additionallypreferably are a phenyl ring or are a 3- to 6-membered unsaturated,partially saturated or saturated heterocycle, the heteroatoms beingselected from the series N, S and O, the phenyl ring or the heterocyclebeing optionally substituted one or more times by identical or differentsubstituents, and the substituents being selectable independently of oneanother from hydrogen, C₁-C₆-alkyl, C₁-C₆-haloalkyl, halogen or cyano,

R⁹, R¹⁰, R¹³, R¹⁴ and R¹⁵ independently of one another more preferablyare optionally singly or multiply identically or differently substitutedmethyl, ethyl, isopropyl or tert-butyl, the substituents beingselectable independently of one another from halogen, cyano, phenyl orpyridyl, where phenyl or pyridyl is optionally substituted one or moretimes by identical or different trifluoromethyl, cyano, fluoro, chloroor trifluoromethoxy substituents,

R⁹, R¹⁰, R¹³, R¹⁴ and R¹⁵ independently of one another additionally morepreferably are phenyl, pyridyl or are a 3- to 6-membered saturatedheterocycle containing 1-2 heteroatoms from the series N, S and O, thephenyl or pyridyl ring or the heterocycle optionally being substitutedone or more times by identical or different substituents, and thesubstituents being selectable independently of one another fromhydrogen, C₁-C₆-alkyl, C₁-C₆-haloalkyl, halogen or cyano,

R¹¹ and R¹² independently of one another preferably are hydrogen or areR⁹,

R¹⁶ preferably is a phenyl ring or is a 5- or 6-membered heteroaromaticring where the heteroatoms are selected from the series N, S and O, thering being optionally substituted one or more times by identical ordifferent substituents, and the substituents being selectableindependently of one another from hydrogen, C₁-C₆-alkyl,C₁-C₆-haloalkyl, halogen, cyano, NO₂, C₁-C₄-alkoxy or C₁-C₄-haloalkoxy,

R¹⁶ more preferably is phenyl, pyridyl, pyrimidinyl, furan or thiophenewhich is optionally substituted one or more times by identical ordifferent substituents, the substituents being selectable independentlyof one another from hydrogen, trifluoromethyl, cyano, fluoro, chloro ortrifluoromethoxy,

R¹⁷ preferably is linear or branched —(C₁-C₄-alkylene)- or is a directbond,

R¹⁷ more preferably is methylene, ethylene, propylene, isopropylene,n-butylene, sec-butylene, isobutylene or a direct bond,

R¹⁷ very preferably is methylene, ethylene or a direct bond,

Q_(Y) preferably is a 5- or 6-membered, partially saturated or saturatedheterocyclic or heteroaromatic ring or an aromatic 8-, 9- or 10-memberedfused heterobicyclic ring system, the heteroatoms being selectable fromthe series N, S and O, the ring or the ring system being optionallysubstituted one or more times by identical or different substituents,and the substituents being selectable independently of one another fromhydrogen, C₁-C₆-alkyl, C₂-C₆-alkenyl, C₂-C₆-alkynyl, C₃-C₆-cycloalkyl,C₁-C₆-haloalkyl, C₂-C₆-haloalkenyl, C₂-C₆-haloalkynyl,C₃-C₆-halocycloalkyl, halogen, CN, CO₂H, CO₂NH₂, NO₂, OH, C₁-C₄-alkoxy,C₁-C₄-haloalkoxy, C₁-C₄-alkylthio, C₁-C₄-alkylsulphinyl,C₁-C₄-alkylsulphonyl, C₁-C₄-haloalkylthio, C₁-C₄-haloalkylsulphinyl andC₁-C₄-haloalkylsulphonyl,

or the substituents being selectable independently of one another fromphenyl or a 5- or 6-membered heteroaromatic ring, where phenyl or thering may optionally be substituted one or more times by identical ordifferent C₁-C₆-alkyl, C₂-C₆-alkenyl, C₂-C₆-alkynyl, C₃-C₆-cycloalkyl,C₁-C₆-haloalkyl, C₂-C₆-haloalkenyl, C₂-C₆-haloalkynyl,C₃-C₆-halocycloalkyl, halogen, CN, NO₂, OH, C₁-C₄-alkoxy orC₁-C₄-haloalkoxy substituents,

Q_(Y) more preferably is an optionally singly or multiply identically ordifferently substituted 5- or 6-membered heteroaromatic ring from theseries Q-1 to Q-53, Q-58 to Q-59, Q-62 to Q-63, an aromatic 9-memberedfused heterobicyclic ring system Q-54 to Q-56 or 5-membered heterocyclicring Q-60 to Q-61, the substituents being selectable independently ofone another from C₁-C₄-alkyl, C₁-C₃-haloalkyl, C₁-C₂-alkoxy, halogen,cyano, hydroxyl, nitro or C₁-C₂-haloalkoxy,

or the substituents being selectable independently of one another fromphenyl or a 5- or 6-membered heteroaromatic ring, where phenyl or thering may optionally be substituted one or more times by identical ordifferent C₁-C₆-alkyl, C₂-C₆-alkenyl, C₂-C₆-alkynyl, C₃-C₆-cycloalkyl,C₁-C₆-haloalkyl, C₂-C₆-haloalkenyl, C₂-C₆-haloalkynyl,C₃-C₆-halocycloalkyl, halogen, CN, NO₂, OH, C₁-C₄-alkoxy orC₁-C₄-haloalkoxy substituents,

Q_(Y) very preferably is an optionally singly or multiply identically ordifferently substituted 5- or 6-membered heteroaromatic ring from theseries Q-36 to Q-40, Q-43, Q-58 to Q-59, Q-62, Q-63, an aromatic9-membered fused heterobicyclic ring system Q-54 to Q-56 or 5-memberedheterocyclic ring Q-60 to Q-61, the substituents being selectableindependently of one another from C₁-C₄-alkyl, C₁-C₃-haloalkyl,C₁-C₂-alkoxy, halogen, cyano, hydroxyl, nitro or C₁-C₂-haloalkoxy,

or the substituents being selectable independently of one another fromphenyl or a 5- or 6-membered heteroaromatic ring, where phenyl or thering may optionally be substituted one or more times by identical ordifferent C₁-C₆-alkyl, C₂-C₆-alkenyl, C₂-C₆-alkynyl, C₃-C₆-cycloalkyl,C₁-C₆-haloalkyl, C₂-C₆-haloalkenyl, C₂-C₆-haloalkynyl,C₃-C₆-halocycloalkyl, halogen, CN, NO₂, C₁-C₄-alkoxy, C₁-C₄-haloalkoxysubstituents,

Q_(Y) more particularly preferably is an optionally singly or multiplyidentically or differently substituted heteroaromatic ring from theseries Q-37, Q-38, Q-39, Q-40, Q43, Q-58, Q-59, Q-62, Q-63, or5-membered heterocyclic ring Q-60, the substituents being selectableindependently of one another from methyl, ethyl, cyclopropyl,tert-butyl, chloro, fluoro, iodo, bromo, cyano, nitro, difluoromethyl,trifluoromethyl, pentafluoroethyl., n-heptafluoropropyl orisoheptafluoropropyl,

or the substituents being selectable independently of one another fromphenyl or a 5- or 6-membered heteroaromatic ring, the substituents beingselectable independently of one another from methyl, ethyl, cyclopropyl,tert-butyl, chloro, fluoro, iodo, bromo, cyano, nitro, difluoromethyl,trifluoromethyl, pentafluorethyl., n-heptafluoropropyl andisoheptafluoropropyl,

The above-recited general radical definitions and elucidations or thoserecited in preference ranges may be combined arbitrarily with oneanother, in other words including combinations between the respectiveranges and preference ranges. They apply to the end products and also tothe precursors and intermediates accordingly.

Preferred in accordance with the invention are the compounds of theformula (I) in which there is a combination of the definitions recitedabove as being preferred (preferably).

Particularly preferred in accordance with the invention are thecompounds of the formula (I) in which there is a combination of thedefinitions recited above as being more preferred.

Very preferred in accordance with the invention are the compounds of theformula (I) in which there is a combination of the definitions recitedabove as being very preferred.

The compounds of the formulae (I) may be present more particularly inthe form of different regioisomers: for example, in the form of mixturesof compounds with the definition Q-62 and/or Q-63, or in the form ofmixtures of Q-58 and 59. The invention therefore also includes mixturesof compounds of the formulae (I) where Q_(Y) has the definitions Q-62and Q-63, and also Q-58 and Q-59, and the compounds may be present indifferent proportions. Preference in this context is given toproportions of the compounds of the formula (I) in which the radicalQ_(Y) is Q-62 or is Q-58 to compounds of the formula (I) in which theradical QY is Q-63 or is Q-59, of 60:40 to 99:1, more preferably of70:30 to 97:3, very preferably of 80:20 to 95:5. More particularlypreferred are the following proportions for a compound of the formula(I) where Q_(Y) has the definition Q-62 or Q-58 to the compound of theformula (I) where Q_(Y) has the definition Q-63 or Q-59: 80:20; 81:19;82:18; 83:17; 84:16; 85:15, 86:14; 87:13; 88:12; 89:11; 90:10, 91:9;92:8; 93:7; 96:6; 95:5.

Preparation Processes

The compounds of the general formula (I) can be obtained by proceduresin which

(A) anilines of the formula (II)

in which R¹, R², R³, R⁴, R⁵, R⁶, X and n are as defined above,

are reacted for example with carbonyl chlorides of the formula (III)

where

Qx, A and Qy are as defined above,

in the presence of an acid-binding agent; or

(B) anilines of the formula (II)

in which R¹, R², R³, R⁴, R⁵, R⁶, X and n are as defined above,

are reacted for example with a carboxylic acid of the formula (IV)

where

Qx, A and Qy are as defined above,

in the presence of a condensing agent; or

(C) for the synthesis of anthranilimides of the formula (I) in which R¹is hydrogen, for example benzoxazinones of the formula (V)

in which R⁵, R⁶, Qx, A, Qy and n are as defined above

are reacted with a hydrazine of the formula (VI)

in which R², R³ and R⁴ are as defined above,

in the presence of a diluent; or

(D) anthranilic hydrazides of the formula (VII)

in which R¹, R², R³, R⁵, R⁶, X, n, Qx, A and Qy are as defined above,

are reacted with a unit Y-R⁴, where R⁴ is as defined above and Yrepresents a suitable leaving group such as halogen or alkoxy;

or

(E) anthranilic hydrazides of the formula (VII)

in which R¹, R², R³, R⁵, R⁶, X, n, Qx, A and Qy are as defined above,

are reacted with an acid anhydride of the general formula (C(═O)—R⁸)₂Oor (C(═O)—OR⁹)₂O

or with an isocyanate of the formula O═C═NR¹¹R¹²,

where R⁸, R⁹, R¹¹ and R¹² are as defined above,

to give compounds of the formula (I) of the invention.

More particularly, compounds of the general formula (I) in which Qx

is where * marks the bond to A,

can be obtained by a procedure in which

(A-1) anilines of the formula (II)

in which R¹, R², R³, R⁴, R⁵, R⁶, X and n are as defined above,

are reacted for example with carbonyl chlorides of the formula (III-1)

in which R⁷, A and Qy are as defined above

in the presence of an acid-binding agent; or

(B-1) anilines of the formula (II)

in which R¹, R², R³, R⁴, R⁵, R⁶, X and n are as defined above,

are reacted, for example, with a carboxylic acid of the formula (IV-1)

in which R⁷, A and Qy are as defined above,

in the presence of a condensing agent; or

(C-1) for synthesis of anthranilamides of the formula (I) in which R¹ ishydrogen, benzoxazinones of the formula (V-1)

in which R⁵, R⁶, R⁷, A, Qy and n are as defined above

are reacted with a hydrazine of the formula (VI)

in which R², R³ and R⁴ are as defined above,

in the presence of a diluent; or

(D) anthranilic hydrazides of the formula (VII-1)

are reacted with a unit Y—R⁴, where R⁴ is as defined above and Yrepresents a suitable leaving group such as halogen or alkoxy,

or

(E) anthranilic hydrazides of the formula (VII-1)

in which R¹, R², R³, R⁵, R⁶, X, n, A and Qy are as defined above,

are reacted with an acid anhydride of the general formula (C(═O)—R⁸)₂Oor (C(═O)—OR⁹)₂O

or with an isocyanate of the formula O═C═NR¹¹R¹²,

where R⁸, R⁹, R¹¹ and R¹² are as defined above,

to give compounds of the formula (I) of the invention.

More particularly, compounds of the general formula (I) in which Qx is

where * marks the bond to A can be prepared by a procedure in which

(B-2) anilines of the formula (II)

in which R¹, R², R³, R⁴, R⁵, R⁶, X and n are as defined above,

are reacted, for example, with a carboxylic acid of the formula (IV-2)

in which R⁷, A and Qy are as defined above,

in the presence of a condensing agent.

Carboxylic acids of the formula (IV-2) are new. They can be prepared bythe reaction scheme below, where R⁷, A and Qy are as defined above and Ris C₁-C₆ alkyl and Hal is halogen, from compounds of the formula (VIII).Compounds of the formula (VIII) are known (e.g. J. Med. Chem. 49, 2006,4721-4736). The reaction of (VIII) to (IX) can be carried out by knownmethods (e.g. WO2005/113506). The further reaction via compounds of theformula X to compounds of the formula (IV-2) can be carried out by knownmethods (e.g. WO2007/144100).

More particularly, compounds of the general formula (I),

in which Qx is

where * marks the bond to A can be prepared by a procedure in which

(B-3) anilines of the formula (II)

in which R¹, R², R³, R⁴, R⁵, R⁶, X and n are as defined above,

are reacted, for example, with a carboxylic acid of the formula (IV-3)

in which R⁷, A and Qy are as defined above

in the presence of a condensing agent.

Carboxylic acids of the formula (IV-3) are new. They can be prepared bythe reaction scheme below, where R⁷, A and Qy are as defined above and Ris C₁-C₆ alkyl and Hal is halogen, from (XI). Compounds of the formula(XI) are known (e.g. J. Med. Chem. 49, 2006, 4721-4736). The reaction of(XI) to (XII) can be carried out by known methods (e.g. WO2005/113506).The further reaction via XIII to carboxylic acids of the formula (IV-3)can be carried out by known methods (e.g. WO2007/144100).

The active ingredients according to the invention, in combination withgood plant tolerance and favourable toxicity to warm-blooded animals andbeing tolerated well by the environment, are suitable for protectingplants and plant organs, for increasing the harvest yields, forimproving the quality of the harvested material and for controllinganimal pests, in particular insects, arachnids, helminths, nematodes andmolluscs, which are encountered in agriculture, in horticulture, inanimal husbandry, in forests, in gardens and leisure facilities, in theprotection of stored products and of materials, and in the hygienesector. They may be preferably employed as plant protection agents. Theyare active against normally sensitive and resistant species and againstall or some stages of development. The abovementioned pests include:

From the order of the Anoplura (Phthiraptera), for example, Damaliniaspp., Haematopinus spp., Linognathus spp., Pediculus spp., Trichodectesspp.

From the class of the Arachnida, for example, Acarus spp., Aceriasheldoni, Aculops spp., Aculus spp., Amblyomma spp., Amphitetranychusviennensis, Argas spp., Boophilus spp., Brevipalpus spp., Bryobiapraetiosa, Chorioptes spp., Dermanyssus gallinae, Eotetranychus spp.,Epitrimerus pyri, Eutetranychus spp., Eriophyes spp., Halotydeusdestructor, Hemitarsonemus spp., Hyalomma spp., Ixodes spp., Latrodectusmactans, Metatetranychus spp., Nuphersa spp., Oligonychus spp.,Ornithodoros spp., Panonychus spp., Phyllocoptruta oleivora,Polyphagotarsonemus latus, Psoroptes spp., Rhipicephalus spp.,Rhizoglyphus spp., Sarcoptes spp., Scorpio maurus, Stenotarsonemus spp.,Tarsonemus spp., Tetranychus spp., Vasates lycopersici.

From the class of the Bivalva, for example, Dreissena spp.

From the order of the Chilopoda, for example, Geophilus spp., Scutigeraspp.

From the order of the Coleoptera, for example, Acalymma vittatum,Acanthoscelides obtectus, Adoretus spp., Agelastica alni, Agriotes spp.,Amphimallon solstitialis, Anobium punctatum, Anoplophora spp.,Anthonomus spp., Anthrenus spp., Apion spp., Apogonia spp., Atomariaspp., Attagenus spp., Bruchidius obtectus, Bruchus spp., Cassida spp.,Cerotoma trifurcata, Ceuthorhynchus spp., Chaetocnema spp., Cleonusmendicus, Conoderus spp., Cosmopolites spp., Costelytra zealandica,Ctenicera spp., Curculio spp., Cryptorhynchus lapathi, Cylindrocopturusspp., Dermestes spp., Diabrotica spp., Dichocrocis spp., Diloboderusspp., Epilachna spp., Epitrix spp., Faustinus spp., Gibbium psylloides,Hellula undalis, Heteronychus arator, Heteronyx spp., Hylamorphaelegans, Hylotrupes bajulus, Hypera postica, Hypothenemus spp.,Lachnosterna consanguinea, Lema spp., Leptinotarsa decemlineata,Leucoptera spp., Lissorhoptrus oryzophilus, Lixus spp., Luperodes spp.,Lyctus spp., Megascelis spp., Melanotus spp., Meligethes aeneus,Melolontha spp., Migdolus spp., Monochamus spp., Naupactusxanthographus, Niptus hololeucus, Oryctes rhinoceros, Oryzaephilussurinamensis, Oryzaphagus oryzae, Otiorrhynchus spp., Oxycetoniajucunda, Phaedon cochleariae, Phyllophaga spp., Phyllotreta spp.,Popillia japonica, Premnotrypes spp., Psylliodes spp., Ptinus spp.,Rhizobius ventralis, Rhizopertha dominica, Sitophilus spp., Sphenophorusspp., Sternechus spp., Symphyletes spp., Tanymecus spp., Tenebriomolitor, Tribolium spp., Trogoderma spp., Tychius spp., Xylotrechusspp., Zabrus spp.

From the order of the Collembola, for example, Onychiurus armatus.

From the order of the Diplopoda, for example, Blaniulus guttulatus.

From the order of the Diptera, for example, Aedes spp., Agromyza spp.,Anastrepha spp., Anopheles spp., Asphondylia spp., Bactrocera spp.,Bibio hortulanus, Calliphora erythrocephala, Ceratitis capitata,Chironomus spp., Chrysomyia spp., Cochliomyia spp., Contarinia spp.,Cordylobia anthropophaga, Culex spp., Cuterebra spp., Dacus oleae,Dasyneura spp., Delia spp., Dermatobia hominis, Drosophila spp.,Echinocnemus spp., Fannia spp., Gastrophilus spp., Hydrellia spp.,Hylemyia spp., Hyppobosca spp., Hypoderma spp., Liriomyza spp., Luciliaspp., Musca spp., Nezara spp., Oestrus spp., Oscinella frit, Pegomyiaspp., Phorbia spp., Prodiplosis spp., Psila rosae, Rhagoletis spp.,Stomoxys spp., Tabanus spp., Tannia spp., Tetanops spp., Tipula spp.

From the class of the Gastropoda, for example, Anion spp., Biomphalariaspp., Bulinus spp., Deroceras spp., Galba spp., Lymnaea spp.,Oncomelania spp., Pomacea spp., Succinea spp.

From the class of the helminths, for example, Ancylostoma duodenale,Ancylostoma ceylanicum, Acylostoma braziliensis, Ancylostoma spp.,Ascaris lubricoides, Ascaris spp., Brugia malayi, Brugia timori,Bunostomum spp., Chabertia spp., Clonorchis spp., Cooperia spp.,Dicrocoelium spp, Dictyocaulus filaria, Diphyllobothrium latum,Dracunculus medinensis, Echinococcus granulosus, Echinococcusmultilocularis, Enterobius vermicularis, Faciola spp., Haemonchus spp.,Heterakis spp., Hymenolepis nana, Hyostrongulus spp., Loa Loa,Nematodirus spp., Oesophagostomum spp., Opisthorchis spp., Onchocercavolvulus, Ostertagia spp., Paragonimus spp., Schistosomen spp.,Strongyloides fuelleborni, Strongyloides stercoralis, Stronyloides spp.,Taenia saginata, Taenia solium, Trichinella spiralis, Trichinellanativa, Trichinella britovi, Trichinella nelsoni, Trichinellapseudopsiralis, Trichostrongulus spp., Trichuris trichuria, Wuchereriabancrofti.

It is furthermore possible to control protozoa, such as Eimeria.

From the order of the Heteroptera, for example, Anasa tristis,Antestiopsis spp., Blissus spp., Calocoris spp., Campylomma livida,Cavelerius spp., Cimex spp., Collaria spp., Creontiades dilutus, Dasynuspiperis, Dichelops furcatus, Diconocoris hewetti, Dysdercus spp.,Euschistus spp., Eurygaster spp., Heliopeltis spp., Horcias nobilellus,Leptocorisa spp., Leptoglossus phyllopus, Lygus spp., Macropesexcavatus, Miridae, Monalonion atratum, Nezara spp., Oebalus spp.,Pentomidae, Piesma quadrata, Piezodorus spp., Psallus seriatus,Pseudacysta persea, Rhodnius spp., Sahlbergella singularis, Scaptocoriscastanea, Scotinophora spp., Stephanitis nashi, Tibraca spp., Triatomaspp.

From the order of the Homoptera, for example, Acyrthosipon spp.,Acrogonia spp., Aeneolamia spp., Agonoscena spp., Aleurodes spp.,Aleurolobus barodensis, Aleurothrixus spp., Amrasca spp., Anuraphiscardui, Aonidiella spp., Aphanostigma pini, Aphis spp., Arboridiaapicalis, Aspidiella spp., Aspidiotus spp., Atanus spp., Aulacorthumsolani, Bemisia spp., Brachycaudus helichrysii, Brachycolus spp.,Brevicoryne brassicae, Calligypona marginata, Carneocephala fulgida,Ceratovacuna lanigera, Cercopidae, Ceroplastes spp., Chaetosiphonfragaefolii, Chionaspis tegalensis, Chlorita onukii, Chromaphisjuglandicola, Chrysomphalus ficus, Cicadulina mbila, Coccomytilus halli,Coccus spp., Cryptomyzus ribis, Dalbulus spp., Dialeurodes spp.,Diaphorina spp., Diaspis spp., Drosicha spp., Dysaphis spp., Dysmicoccusspp., Empoasca spp., Eriosoma spp., Erythroneura spp., Euscelisbilobatus, Ferrisia spp., Geococcus coffeae, Hieroglyphus spp.,Homalodisca coagulata, Hyalopterus arundinis, Icerya spp., Idiocerusspp., Idioscopus spp., Laodelphax striatellus, Lecanium spp.,Lepidosaphes spp., Lipaphis erysimi, Macrosiphum spp., Mahanarva spp.,Melanaphis sacchari, Metcalfiella spp., Metopolophium dirhodum, Monelliacostalis, Monelliopsis pecanis, Myzus spp., Nasonovia ribisnigri,Nephotettix spp., Nilaparvata lugens, Oncometopia spp., Ortheziapraelonga, Parabemisia myricae, Paratrioza spp., Parlatoria spp.,Pemphigus spp., Peregrinus maidis, Phenacoccus spp., Phloeomyzuspasserinii, Phorodon humuli, Phylloxera spp., Pinnaspis aspidistrae,Planococcus spp., Protopulvinaria pyriformis, Pseudaulacaspis pentagona,Pseudococcus spp., Psylla spp., Pteromalus spp., Pyrilla spp.,Quadraspidiotus spp., Quesada gigas, Rastrococcus spp., Rhopalosiphumspp., Saissetia spp., Scaphoides titanus, Schizaphis graminum,Selenaspidus articulatus, Sogata spp., Sogatella furcifera, Sogatodesspp., Stictocephala festina, Tenalaphara malayensis, Tinocalliscaryaefoliae, Tomaspis spp., Toxoptera spp., Trialeurodes spp., Triozaspp., Typhlocyba spp., Unaspis spp., Viteus vitifolii, Zygina spp.

From the order of the Hymenoptera, for example, Athalia spp., Diprionspp., Hoplocampa spp., Lasius spp., Monomorium pharaonis, Vespa spp.

From the order of the Isopoda, for example, Armadillidium vulgare,Oniscus asellus, Porcellio scaber.

From the order of the Isoptera, for example, Acromyrmex spp., Atta spp.,Cornitermes cumulans, Microtermes obesi, Odontotermes spp.,Reticulitermes spp.

From the order of the Lepidoptera, for example, Acronicta major,Adoxophyes spp., Aedia leucomelas, Agrotis spp., Alabama spp., Amyeloistransitella, Anarsia spp., Anticarsia spp., Argyroploce spp., Barathrabrassicae, Borbo cinnara, Bucculatrix thurberiella, Bupalus piniarius,Bus seola spp., Cacoecia spp., Caloptilia theivora, Capua reticulana,Carpocapsa pomonella, Carposina niponensis, Cheimatobia brumata, Chilospp., Choristoneura spp., Clysia ambiguella, Cnaphalocerus spp.,Cnephasia spp., Conopomorpha spp., Conotrachelus spp., Copitarsia spp.,Cydia spp., Dalaca noctuides, Diaphania spp., Diatraea saccharalis,Earias spp., Ecdytolopha aurantium, Elasmopalpus lignosellus, Eldanasaccharina, Ephestia kuehniella, Epinotia spp., Epiphyas postvittana,Etiella spp., Eulia spp., Eupoecilia ambiguella, Euproctis spp., Euxoaspp., Feltia spp., Galleria mellonella, Gracillaria spp., Grapholithaspp., Hedylepta spp., Helicoverpa spp., Heliothis spp., Hofmannophilapseudospretella, Homoeosoma spp., Homona spp., Hyponomeuta padella,Kakivoria flavofasciata, Laphygma spp., Laspeyresia molesta, Leucinodesorbonalis, Leucoptera spp., Lithocolletis spp., Lithophane antennata,Lobesia spp., Loxagrotis albicosta, Lymantria spp., Lyonetia spp.,Malacosoma neustria, Maruca testulalis, Mamestra brassicae, Mocis spp.,Mythimna separata, Nymphula spp., Oiketicus spp., Oria spp., Orthagaspp., Ostrinia spp., Oulema oryzae, Panolis flammea, Parnara spp.,Pectinophora spp., Perileucoptera spp., Phthorimaea spp., Phyllocnistiscitrella, Phyllonorycter spp., Pieris spp., Platynota stultana, Plusiaspp., Plutella xylostella, Prays spp., Prodenia spp., Protoparce spp.,Pseudaletia spp., Pseudoplusia includens, Pyrausta nubilalis,Rachiplusia nu, Schoenobius spp., Scirpophaga spp., Scotia segetum,Sesamia spp., Sparganothis spp., Spodoptera spp., Stathmopoda spp.,Stomopteryx subsecivella, Synanthedon spp., Tecia solanivora, Thermesiagemmatalis, Tinea pellionella, Tineola bisselliella, Tortrix viridana,Trichoplusia spp., Tuta absoluta, Virachola spp.

From the order of the Orthoptera, for example, Acheta domesticus, Blattaorientalis, Blattella germanica, Dichroplus spp., Gryllotalpa spp.,Leucophaea maderae, Locusta spp., Melanoplus spp., Periplanetaamericana, Schistocerca gregaria.

From the order of the Siphonaptera, for example, Ceratophyllus spp.,Xenopsylla cheopis.

From the order of the Symphyla, for example, Scutigerella spp.

From the order of the Thysanoptera, for example, Anaphothrips obscurus,Baliothrips biformis, Drepanothris reuteri, Enneothrips flavens,Frankliniella spp., Heliothrips spp., Hercinothrips femoralis,Rhipiphorothrips cruentatus, Scirtothrips spp., Taeniothrips cardamoni,Thrips spp.

From the order of the Thysanura, for example, Lepisma saccharina.

The phytoparasitic nematodes include, for example, Aphelenchoides spp.,Bursaphelenchus spp., Ditylenchus spp., Globodera spp., Heterodera spp.,Longidorus spp., Meloidogyne spp., Pratylenchus spp., Radopholussimilis, Trichodorus spp., Tylenchulus semipenetrans, Xiphinema spp.

If appropriate, the compounds according to the invention can, at certainconcentrations or application rates, also be used as herbicides,safeners, growth regulators or agents to improve plant properties, or asmicrobicides, for example as fungicides, antimycotics, bactericides,viricides (including agents against viroids) or as agents against MLO(mycoplasma-like organisms) and RLO (rickettsia-like organisms). Ifappropriate, they can also be employed as intermediates or precursorsfor the synthesis of other active ingredients.

The active ingredients can be converted to the customary formulations,such as solutions, emulsions, wettable powders, water- and oil-basedsuspensions, powders, dusts, pastes, soluble powders, soluble granules,granules for broadcasting, suspension-emulsion concentrates, naturalmaterials impregnated with active ingredient, synthetic materialsimpregnated with active ingredient, fertilizers and microencapsulationsin polymeric substances.

These formulations are produced in a known manner, for example by mixingthe active ingredients with extenders, that is liquid solvents and/orsolid carriers, optionally with the use of surfactants, that isemulsifiers and/or dispersants and/or foam-formers. The formulations areprepared either in suitable apparatuses or else before or during theapplication.

Suitable for use as auxiliaries are substances which are suitable forimparting to the composition itself and/or to preparations derivedtherefrom (for example spray liquors, seed dressings) particularproperties, such as certain technical properties and/or else particularbiological properties. Typical suitable auxiliaries are: extenders,solvents and carriers.

Suitable extenders are, for example, water, polar and nonpolar organicchemical liquids, for example from the classes of the aromatic andnon-aromatic hydrocarbons (such as paraffins, alkylbenzenes,alkylnaphthalenes, chlorobenzenes), the alcohols and polyols (which, ifappropriate, may also be substituted, etherified and/or esterified), theketones (such as acetone, cyclohexanone), esters (including fats andoils) and (poly)ethers, the unsubstituted and substituted amines,amides, lactams (such as N-alkylpyrrolidones) and lactones, thesulphones and sulphoxides (such as dimethyl sulphoxide).

If the extender used is water, it is also possible to employ, forexample, organic solvents as auxiliary solvents. Essentially, suitableliquid solvents are: aromatics such as xylene, toluene oralkylnaphthalenes, chlorinated aromatics and chlorinated aliphatichydrocarbons such as chlorobenzenes, chloroethylenes or methylenechloride, aliphatic hydrocarbons such as cyclohexane or paraffins, forexample petroleum fractions, mineral and vegetable oils, alcohols suchas butanol or glycol and also their ethers and esters, ketones such asacetone, methyl ethyl ketone, methyl isobutyl ketone or cyclohexanone,strongly polar solvents such as dimethyl sulphoxide, and also water.

Suitable solid carriers are:

for example, ammonium salts and ground natural minerals such as kaolins,clays, talc, chalk, quartz, attapulgite, montmorillonite or diatomaceousearth, and ground synthetic minerals, such as finely divided silica,alumina and silicates; suitable solid carriers for granules are: forexample, crushed and fractionated natural rocks such as calcite, marble,pumice, sepiolite and dolomite, and also synthetic granules of inorganicand organic meals, and granules of organic material such as paper,sawdust, coconut shells, maize cobs and tobacco stalks; suitableemulsifiers and/or foam-formers are: for example, nonionic and anionicemulsifiers, such as polyoxyethylene fatty acid esters, polyoxyethylenefatty alcohol ethers, for example alkylaryl polyglycol ethers,alkylsulphonates, alkyl sulphates, arylsulphonates and also proteinhydrolysates; suitable dispersants are nonionic and/or ionic substances,for example from the classes of the alcohol-POE and/or -POP ethers, acidand/or POP-POE esters, alkylaryl and/or POP-POE ethers, fat and/orPOP-POE adducts, POE- and/or POP-polyol derivatives, POE- and/orPOP-sorbitan or -sugar adducts, alkyl or aryl sulphates, alkyl- orarylsulphonates and alkyl or aryl phosphates or the correspondingPO-ether adducts. Furthermore, suitable oligo- or polymers, for examplethose derived from vinylic monomers, from acrylic acid, from EO and/orPO alone or in combination with, for example, (poly)alcohols or(poly)amines. It is also possible to employ lignin and its sulphonicacid derivatives, unmodified and modified celluloses, aromatic and/oraliphatic sulphonic acids and their adducts with formaldehyde.

Tackifiers such as carboxymethylcellulose, natural and syntheticpolymers in the form of powders, granules or latices, such as gumarabic, polyvinyl alcohol and polyvinyl acetate, as well as naturalphospholipids such as cephalins and lecithins, and syntheticphospholipids, can be used in the formulations.

It is possible to use colorants such as inorganic pigments, for exampleiron oxide, titanium oxide and Prussian Blue, and organic dyestuffs,such as alizarin dyestuffs, azo dyestuffs and metal phthalocyaninedyestuffs, and trace nutrients such as salts of iron, manganese, boron,copper, cobalt, molybdenum and zinc.

Other possible additives are perfumes, mineral or vegetable, optionallymodified oils, waxes and nutrients (including trace nutrients), such assalts of iron, manganese, boron, copper, cobalt, molybdenum and zinc.

Stabilizers, such as low-temperature stabilizers, preservatives,antioxidants, light stabilizers or other agents which improve chemicaland/or physical stability may also be present.

The formulations generally comprise between 0.01 and 98% by weight ofactive ingredient, preferably between 0.5 and 90%.

The active ingredient of the invention may be present, in its commercialformulations and in the appropriate forms prepared from theseformulations, in a mixture with other active ingredients such asinsecticides, attractants, sterilants, bactericides, acaricides,nematicides, fungicides, growth regulators, herbicides, safeners,fertilizers and semiochemicals. In particular the active ingredients ofthe invention may be used in combination with further (auxiliary) agentsfor boosting activity.

When used as insecticides, the active ingredients according to theinvention can furthermore be present, in their commercially availableformulations and in the application forms prepared from theseformulations, as a mixture with synergists. Synergists are compoundswhich increase the action of the active ingredients without it beingnecessary for the synergistic agent added to be active itself.

When used as insecticides, the active ingredients according to theinvention can furthermore be present, in their commercially availableformulations and in the application forms prepared from theseformulations, as mixtures with inhibitors which reduce degradation ofthe active ingredient after use in the environment of the plant, on thesurface of parts of plants or in plant tissues.

The active ingredient content of the application forms prepared from thecommercially available formulations can vary within wide ranges. Theactive ingredient concentration of the application forms can be from0.00000001 to 95% by weight of active ingredient, preferably between0.00001 and 1% by weight.

The compounds are employed in a customary manner appropriate for theapplication forms.

All plants and plant parts can be treated in accordance with theinvention. Plants are to be understood as meaning in the present contextall plants and plant populations such as desired and undesired wildplants or crop plants (including naturally occurring crop plants). Cropplants can be plants which can be obtained by conventional plantbreeding and optimization methods or by biotechnological and geneticengineering methods or by combinations of these methods, including thetransgenic plants and including the plant cultivars protectable or notprotectable by plant breeders' rights. Plant parts are to be understoodas meaning all parts and organs of plants above and below the ground,such as shoot, leaf, flower and root, examples which may be mentionedbeing leaves, needles, stalks, stems, flowers, fruit bodies, fruits,seeds, roots, tubers and rhizomes. The plant parts also includeharvested material, and vegetative and generative propagation material,for example cuttings, tubers, rhizomes, offshoots and seeds.

Treatment according to the invention of the plants and plant parts withthe active ingredients is carried out directly or by allowing the activeingredients to act on the surroundings, habitat or storage space by thecustomary treatment methods, for example by immersion, spraying,evaporation, fogging, scattering, painting on, injection and, in thecase of propagation material, in particular in the case of seeds, alsoby applying one or more coats.

As already mentioned above, it is possible to treat all plants and theirparts according to the invention. In a preferred embodiment, wild plantspecies and plant cultivars, or those obtained by conventionalbiological breeding methods, such as crossing or protoplast fusion, andparts thereof, are treated. In a further preferred embodiment,transgenic plants and plant cultivars obtained by genetic engineeringmethods, if appropriate in combination with conventional methods(Genetically Modified Organisms), and parts thereof are treated. Theterms “parts”, “parts of plants” and “plant parts” have been explainedabove.

Particularly preferably, plants of the plant cultivars which are in eachcase commercially available or in use are treated according to theinvention. Plant cultivars are to be understood as meaning plants havingnovel properties (“traits”) which have been obtained by conventionalbreeding, by mutagenesis or by recombinant DNA techniques. These can becultivars, bio- or genotypes.

Depending on the plant species or plant cultivars, their location andgrowth conditions (soils, climate, vegetation period, diet), thetreatment according to the invention may also result in superadditive(“synergistic”) effects. Thus, for example, reduced application ratesand/or a widening of the activity spectrum and/or an increase in theactivity of the substances and compositions which can be used accordingto the invention, better plant growth, increased tolerance to high orlow temperatures, increased tolerance to drought or to water or soilsalt content, increased flowering performance, easier harvesting,accelerated maturation, higher harvest yields, higher quality and/or ahigher nutritional value of the harvested products, better storagestability and/or processability of the harvested products are possible,which exceed the effects which were actually to be expected.

The transgenic plants or plant cultivars (obtained by geneticengineering) which are preferably to be treated according to theinvention include all plants which, by virtue of the geneticmodification, received genetic material which imparts particularlyadvantageous, useful traits to these plants. Examples of such traits arebetter plant growth, increased tolerance to high or low temperatures,increased tolerance to drought or to water or soil salt content,increased flowering performance, easier harvesting, acceleratedmaturation, higher harvest yields, higher quality and/or a highernutritional value of the harvested products, better storage stabilityand/or processability of the harvested products. Further andparticularly emphasized examples of such traits are a better defence ofthe plants against animal and microbial pests, such as against insects,mites, phytopathogenic fungi, bacteria and/or viruses, and alsoincreased tolerance of the plants to certain herbicidally activeingredients. Examples of transgenic plants which may be mentioned arethe important crop plants, such as cereals (wheat, rice), maize, soyabeans, potatoes, sugar beet, tomatoes, peas and other vegetablevarieties, cotton, tobacco, oilseed rape and also fruit plants (with thefruits apples, pears, citrus fruits and grapes), and particular emphasisis given to maize, soya beans, potatoes, cotton, tobacco and oilseedrape.

Traits that are emphasized in particular are increased defence of theplants against insects, arachnids, nematodes and slugs and snails byvirtue of toxins formed in the plants, in particular those formed in theplants by the genetic material from Bacillus thuringiensis (for exampleby the genes CryIA(a), CryIA(b), CryIA(c), CryIIA, CryIIIA, CryIIIB2,Cry9c, Cry2Ab, Cry3Bb and CryIF and also combinations thereof) (referredto hereinbelow as “Bt plants”). Traits that are also particularlyemphasized are the increased defence of the plants against fungi,bacteria and viruses by systemic acquired resistance (SAR), systemin,phytoalexins, elicitors and resistance genes and correspondinglyexpressed proteins and toxins. Traits that are furthermore particularlyemphasized are the increased tolerance of the plants to certainherbicidally active ingredients, for example imidazolinones,sulphonylureas, glyphosate or phosphinotricin (for example the “PAT”gene). The genes which impart the desired traits in question can also bepresent in combination with one another in the transgenic plants.Examples of “Bt plants” which may be mentioned are maize varieties,cotton varieties, soya bean varieties and potato varieties which aresold under the trade names YIELD GARD® (for example maize, cotton, soyabeans), KnockOut® (for example maize), StarLink® (for example maize),Bollgard® (cotton), Nucotn® (cotton) and NewLeaf® (potato). Examples ofherbicide-tolerant plants which may be mentioned are maize varieties,cotton varieties and soya bean varieties which are sold under the tradenames Roundup Ready® (tolerance to glyphosate, for example maize,cotton, soya beans), Liberty Link® (tolerance to phosphinotricin, forexample oilseed rape), IMI® (tolerance to imidazolinones) and STS®(tolerance to sulphonylureas, for example maize). Herbicide-resistantplants (plants bred in a conventional manner for herbicide tolerance)which may be mentioned include the varieties sold under the nameClearfield® (for example maize). Of course, these statements also applyto plant cultivars having these genetic traits or genetic traits stillto be developed, which plant cultivars will be developed and/or marketedin the future.

The plants listed can be treated according to the invention in aparticularly advantageous manner with the compounds of the generalformula I and/or the active ingredient mixtures according to theinvention. The preferred ranges stated above for the active ingredientsor mixtures also apply to the treatment of these plants. Particularemphasis is given to the treatment of plants with the compounds ormixtures specifically mentioned in the present text.

The active ingredients according to the invention are active not onlyagainst plant pests, hygiene pests and stored-product pests but also inthe veterinary field against animal parasites (ecto and endoparasites)such as hard ticks, soft ticks, scab mites, harvest mites, flies(stinging and licking), parasitic fly larvae, lice, hair lice, bird liceand fleas. These parasites include:

from the order of the Anoplurida, for example Haematopinus spp.,Linognathus spp., Pediculus spp., Phtirus spp., Solenopotes spp.

from the order of the Mallophagida and the suborders Amblycerina andIschnocerina, for example Trimenopon spp., Menopon spp., Trinoton spp.,Bovicola spp., Werneckiella spp., Lepikentron spp., Damalina spp.,Trichodectes spp., Felicola spp.

from the order of the Diptera and the suborders Nematocerina andBrachycerina, for example Aedes spp., Anopheles spp., Culex spp.,Simulium spp., Eusimulium spp., Phlebotomus spp., Lutzomyia spp.,Culicoides spp., Chrysops spp., Hybomitra spp., Atylotus spp., Tabanusspp., Haematopota spp., Philipomyia spp., Braula spp., Musca spp.,Hydrotaea spp., Stomoxys spp., Haematobia spp., Morellia spp., Fanniaspp., Glossina spp., Calliphora spp., Lucilia spp., Chrysomyia spp.,Wohlfahrtia spp., Sarcophaga spp., Oestrus spp., Hypoderma spp.,Gasterophilus spp., Hippobosca spp., Lipoptena spp., Melophagus spp.

from the order of the Siphonapterida, for example Pulex spp.,Ctenocephalides spp., Xenopsylla spp., Ceratophyllus spp.

from the order of the Heteropterida, for example Cimex spp., Triatomaspp., Rhodnius spp., Panstrongylus spp.

from the order of the Blattarida, for example Blatta orientalis,Periplaneta americana, Blattela germanica, Supella spp.

from the subclass of the Acari (Acarina) and the orders of the Meta- andMesostigmata, for example Argas spp., Ornithodorus spp., Otobius spp.,Ixodes spp., Amblyomma spp., Boophilus spp., Dermacentor spp.,Haemophysalis spp., Hyalomma spp., Rhipicephalus spp., Dermanyssus spp.,Raillietia spp., Pneumonys sus spp., Sternostoma spp., Varroa spp.

from the order of the Actinedida (Prostigmata) and Acaridida(Astigmata), for example Acarapis spp., Cheyletiella spp.,Ornithocheyletia spp., Myobia spp., Psorergates spp., Demodex spp.,Trombicula spp., Listrophorus spp., Acarus spp., Tyrophagus spp.,Caloglyphus spp., Hypodectes spp., Pterolichus spp., Psoroptes spp.,Chorioptes spp., Otodectes spp., Sarcoptes spp., Notoedres spp.,Knemidocoptes spp., Cytodites spp., Laminosioptes spp.

The active ingredients of the formula (I) according to the invention arealso suitable for controlling arthropods, agricultural livestock suchas, for example, cattle, sheep, goats, horses, pigs, donkeys, camels,buffaloes, rabbits, chickens, turkeys, ducks, geese, honeybees, otherdomestic animals such as, for example, dogs, cats, cage birds, aquariumfish and what are known as experimental animals such as, for example,hamsters, guinea pigs, rats and mice. By controlling these arthropods itis intended to reduce deaths and improve performance (in the case ofmeat, milk, wool, hides, eggs, honey and the like) so that moreeconomical and simpler animal keeping is made possible by the use of theactive ingredients according to the invention.

In the veterinary field and in animal keeping, the active ingredientsaccording to the invention are applied in the known manner by enteraladministration in the form of, for example, tablets, capsules, drinks,drenches, granules, pastes, boluses, the feed-through method,suppositories, by parenteral administration, such as, for example, byinjections (intramuscular, subcutaneous, intravenous, intraperitonealand the like), implants, by nasal application, by dermal application inthe form of, for example, bathing or dipping, spraying, pouring-on andspotting-on, washing, dusting, and with the aid ofactive-ingredient-comprising shaped articles such as collars, ear tags,tail tags, limb bands, halters, marking devices and the like.

When used for livestock, poultry, domestic animals and the like, theactive ingredients of the formula (I) can be applied as formulations(for example powders, emulsions, flowables) which comprise the activeingredients in an amount of from 1 to 80% by weight, either directly orafter 100- to 10 000-fold dilution, or they can be used as a chemicalbath.

It has furthermore been found that the compounds according to theinvention also have a strong insecticidal action against insects whichdestroy industrial materials.

The following insects may be mentioned as examples and as preferred—butwithout any limitation:

Beetles, such as Hylotrupes bajulus, Chlorophorus pilosis, Anobiumpunctatum, Xestobium rufovillosum, Ptilinus pecticornis, Dendrobiumpertinex, Ernobius mollis, Priobium carpini, Lyctus brunneus, Lyctusafricanus, Lyctus planicollis, Lyctus linearis, Lyctus pubescens,Trogoxylon aequale, Minthes rugicollis, Xyleborus spec. Tryptodendronspec. Apate monachus, Bostrychus capucins, Heterobostrychus brunneus,Sinoxylon spec. Dinoderus minutus;

Hymenopterons, such as Sirex juvencus, Urocerus gigas, Urocerus gigastaignus, Urocerus augur;

Termites, such as Kalotermes flavicollis, Cryptotermes brevis,Heterotermes indicola, Reticulitermes flavipes, Reticulitermessantonensis, Reticulitermes lucifugus, Mastotermes darwiniensis,Zootermopsis nevadensis, Coptotermes formosanus;

Bristletails, such as Lepisma saccharina.

Industrial materials in the present connection are to be understood asmeaning non-living materials, such as, preferably, plastics, adhesives,sizes, papers and cardboards, leather, wood and processed wood productsand coating compositions.

The ready-to-use compositions may, if appropriate, comprise furtherinsecticides and, if appropriate, one or more fungicides.

With respect to possible additional mixing partners, reference is madeto the abovementioned insecticides and fungicides.

The compounds according to the invention can likewise be employed forprotecting objects which come into contact with saltwater or brackishwater, in particular hulls, screens, nets, buildings, moorings andsignalling systems, against fouling.

Furthermore, the compounds according to the invention, alone or incombinations with other active ingredients, may be employed asantifouling agents.

In domestic, hygiene and stored-product protection, the activeingredients are also suitable for controlling animal pests, inparticular insects, arachnids and mites, which are found in enclosedspaces such as, for example, dwellings, factory halls, offices, vehiclecabins and the like. They can be employed alone or in combination withother active ingredients and auxiliaries in domestic insecticideproducts for controlling these pests. They are active against sensitiveand resistant species and against all developmental stages. These pestsinclude:

From the order of the Scorpionidea, for example, Buthus occitanus.

From the order of the Acarina, for example, Argas persicus, Argasreflexus, Bryobia ssp., Dermanyssus gallinae, Glyciphagus domesticus,Ornithodorus moubat, Rhipicephalus sanguineus, Trombicula alfreddugesi,Neutrombicula autumnalis, Dermatophagoides pteronissimus,Dermatophagoides forinae.

From the order of the Araneae, for example, Aviculariidae, Araneidae.

From the order of the Opiliones, for example, Pseudoscorpiones chelifer,Pseudoscorpiones cheiridium, Opiliones phalangium.

From the order of the Isopoda, for example, Oniscus asellus, Porcellioscaber.

From the order of the Diplopoda, for example, Blaniulus guttulatus,Polydesmus spp.

From the order of the Chilopoda, for example, Geophilus spp.

From the order of the Zygentoma, for example, Ctenolepisma spp., Lepismasaccharina, Lepismodes inquilinus.

From the order of the Blattaria, for example, Blatta orientalies,Blattella germanica, Blattella asahinai, Leucophaea maderae, Panchloraspp., Parcoblatta spp., Periplaneta australasiae, Periplaneta americana,Periplaneta brunnea, Periplaneta fuliginosa, Supella longipalpa.

From the order of the Saltatoria, for example, Acheta domesticus.

From the order of the Dermaptera, for example, Forficula auricularia.

From the order of the Isoptera, for example, Kalotermes spp.,Reticulitermes spp.

From the order of the Psocoptera, for example, Lepinatus spp.,Liposcelis spp.

From the order of the Coleoptera, for example, Anthrenus spp., Attagenusspp., Dermestes spp., Latheticus oryzae, Necrobia spp., Ptinus spp.,Rhizopertha dominica, Sitophilus granarius, Sitophilus oryzae,Sitophilus zeamais, Stegobium paniceum.

From the order of the Diptera, for example, Aedes aegypti, Aedesalbopictus, Aedes taeniorhynchus, Anopheles spp., Calliphoraerythrocephala, Chrysozona pluvialis, Culex quinquefasciatus, Culexpipiens, Culex tarsalis, Drosophila spp., Fannia canicularis, Muscadomestica, Phlebotomus spp., Sarcophaga carnaria, Simulium spp.,Stomoxys calcitrans, Tipula paludosa.

From the order of the Lepidoptera, for example, Achroia grisella,Galleria mellonella, Plodia interpunctella, Tinea cloacella, Tineapellionella, Tineola bisselliella.

From the order of the Siphonaptera, for example, Ctenocephalides canis,Ctenocephalides felis, Pulex irritans, Tunga penetrans, Xenopsyllacheopis.

From the order of the Hymenoptera, for example, Camponotus herculeanus,Lasius fuliginosus, Lasius niger, Lasius umbratus, Monomorium pharaonis,Paravespula spp., Tetramorium caespitum.

From the order of the Anoplura, for example, Pediculus humanus capitis,Pediculus humanus corporis, Pemphigus spp., Phylloera vastatrix,Phthirus pubis.

From the order of the Heteroptera, for example, Cimex hemipterus, Cimexlectularius, Rhodinus prolixus, Triatoma infestans.

In the field of domestic insecticides, they are used alone or incombination with other suitable active ingredients, such as phosphoricesters, carbamates, pyrethroids, neonicotinoids, growth regulators oractive ingredients from other known classes of insecticides.

They are used in aerosols, unpressurized spray products, for examplepump and atomizer sprays, automatic fogging systems, foggers, foams,gels, evaporator products with evaporator tablets made of cellulose orpolymer, liquid evaporators, gel and membrane evaporators,propeller-driven evaporators, non-energized, or passive, evaporationsystems, moth papers, moth bags and moth gels, as granules or dusts, inbaits for scattering or in bait stations.

DESCRIPTION OF THE PREPARATION PROCESSES AND INTERMEDIATES

Anilines of the formula (II) are known (e.g. WO2007/043677,WO2008/126858, WO2008/126933) or can be prepared by known methods.

Carbonyl chlorides of the formula (III) in which Qx is pyrazole areknown (e.g. WO2007/144100) or can be prepared by known methods.

Carboxylic acids of the formula (IV) in which Qx is pyrazole are known(e.g. WO2007/144100) or can be prepared by known methods.

Benzoxazinones of the formula (V) in which Qx is pyrazole are known(e.g. WO2007/144100) or can be prepared by known methods.

Hydrazines of the formula (VI) are known (e.g. WO2007/043677,WO2008/126858, WO2008/126933) or can be prepared by known methods.

Anthranilic hydrazides of the formula (VII) are new. They can beprepared in accordance with process C.

PREPARATION EXAMPLES Synthesis of Carboxylic Acids of the Formula (IV-2)Example A: (IX) Synthesis of ethyl2-(bromomethyl)-4-(2-chlorophenyl)pyrimidine-5-carboxylate

An amount of 820 mg (2.96 mmol) of ethyl4-(2-chlorophenyl)-2-methylpyrimidine-5-carboxylate and 633 mg (3.55mmol) of N-bromosuccinimide were dissolved in 18 ml of carbontetrachloride and heated with stirring to boiling. At the heat ofboiling, in portions, 49 mg (0.29 mmol) of2,2′-azobis-2-methylpropanenitrile were added over 5 hours, followed byrefluxing for a further hour. After cooling to room temperature, thereaction solution was filtered and the mother liquor was freed from thesolvent under reduced pressure. The desired product was isolated bychromatographic purification.

(log P: 3.32; MH⁺: 357; ¹H-NMR (400 MHz, DMSO, δ, ppm): 1.00 (t, 3H),4.12 (q, 2H), 4.80 (s, 2H), 7.50 (m, 4 H), 9.30 (s, 1H).

Example B: (X) Synthesis of ethyl4-(2-chlorophenyl)-2-{[5-(trifluoromethyl)-2H-tetrazol-2-yl]methyl}-pyrimidine-5-carboxylate

An amount of 345 mg (0.97 mmol) of ethyl2-(bromomethyl)-4-(2-chlorophenyl)pyrimidine-5-carboxylate was added toa solution of 200 mg (1.45 mmol) of trifluoromethyltetrazole in 10 ml ofacetonitrile. Then 174 mg (1.26 mmol) of potassium carbonate were addedto the reaction solution, which was stirred at 60° C. for 6 hours. Aftercooling to room temperature, the reaction solution was filtered and themother liquor was freed from the solvent under reduced pressure. Theresidue was admixed with 10 ml of water and extracted with ethyl acetate(3×20 ml). The combined organic phases were dried over sodium sulphate.The solvent was removed under reduced pressure and the residue waspurified by chromatography.

(log P: 3.56; MH⁺: 413; ¹H-NMR (400 MHz, DMSO, δ, ppm): 0.99 (t, 3H),4.13 (q, 2H) 6.62 (s, 2H), 7.50 (m, 4 H), 9.28 (s, 1H).

Example C: (IV-2) Synthesis of4-(2-chlorophenyl)-2-{[5-(trifluoromethyl)-2H-tetrazol-2-yl]methyl}pyrimidine-5-carboxylicacid

An amount of 1.74 g (4.21 mmol) of ethyl4-(2-chlorophenyl)-2-{[5-(trifluoromethyl)-2H-tetrazol-2-yl]methyl}pyrimidine-5-carboxylatewas dissolved in 12 ml of ethanol and the solution was admixed dropwiseat 0° C. with 45% strength aqueous sodium hydroxide solution (5.05mmol). The reaction was stirred for a further hour and warmed to RT. Theethanol was then removed under reduced pressure and the residue wasadmixed with ice-water (10 ml). The aqueous phase was extracted withethyl acetate. The organic phase was discarded. Then the aqueous phasewas adjusted to a pH of 3 using hydrochloric acid, and again extractedwith ethyl acetate (3×20 ml). The combined organic phases were driedover sodium sulphate.

(log P: 2.50; MH⁺: 385; ¹H-NMR (400 MHz, DMSO, δ, ppm): 6.59 (s, 2H),7.48 (m, 4H), 9.27 (s, 1H).

PREPARATION EXAMPLES

The preparation processes described above can be used to give thecompounds of the formula (I)—for example the following compounds of theformula (I):

Example 1 Synthesis of methylN′-(5-chloro-2-{[2-(3-chloropyridin-2-yl)-5-(5-heptalluoropropyltetrazol-2-ylmethyl)-2H-pyrazole-3-carbonyl]amino}-3-methylbenzoyl)-N-methylhydrazinecarboxylate

An amount of 250 mg (0.40 mmol) of6-chloro-2-[2-(3-chloropyridin-2-yl)-5-(5-heptafluoropropyltetrazol-2-ylmethyl)-2H-pyrazol-3-yl]-8-methyl-3,1-benzoxazin-4-onewas dissolved in 20 ml of tetrahydrofuran and admixed with 209 mg (2.06mmol) of methyl N-methylhydrazinecarboxylate. The mixture was firststirred at room temperature for 3 h and then heated under reflux for 16h.

After cooling, the reaction mixture was freed from the solvent underreduced pressure. The desired product was isolated by chromatographicpurification of the residue (log P: 3.66; MH⁺: 727; ¹H-NMR (400 MHz,DMSO, δ, ppm): 2.07 (s, 3H), 2.88 (s, 3H), 3.45 (br s, 3H), 6.35 (s,2H), 7.29 (bs, 1H), 7.38 (s, 1H), 7.54 (d, 1H), 7.58 (dd, 1H), 8.13 (dd,1H), 8.45 (dd, 1H), 10.24 (s, 1H), 10.46 (s, 1H)).

Example 2 MethylN′-(2-{[2-(3-chloropyridin-2-yl)-5-(5-heptalluoropropyltetrazol-2-ylmethyl)-2H-pyrazole-3-carbonyl]amino}-5-iodo-3-methylbenzoyl)hydrazincarboxylate

An amount of 583 mg (0.78 mmol) ofN-(2-hydrazinocarbonyl-4-iodo-6-methylphenyl)-2-(3-chloropyridin-2-yl)-5-(5-heptafluoropropyltetrazol-2-ylmethyl)-2H-pyrazole-3-carboxamidewas dissolved in 25 ml of pyridine and the solution was admixed dropwisewith 84 mg (0.89 mmol) of methyl chloroformate. The mixture was stirredat room temperature for 2 h and freed from the solvent under reducedpressure. The desired product was isolated by chromatographicpurification of the residue (log P: 3.58; MH⁺: 805; ¹H-NMR (400 MHz,DMSO, δ, ppm): 2.10 (s, 3H), 3.59 (br s, 3H), 6.34 (s, 2H), 7.34 (s,1H), 7.58 (dd, 1H), 7.68 (br s, 1H), 7.81 (d, 1H), 8.14 (dd, 1H), 8.47(dd, 1H), 9.24 (bs, 1H), 10.08 (s, 1H), 10.18 (s, 1H)).

The following examples can be obtained analogously:

The table gives, for Example 1, the complete NMR signals, and for thefurther examples a combination of log P, mass (MH⁺) and those NMRsignals which relate to the part of the molecule introduced last in theprocess.

¹H-NMR (400 MHz, DMSO, Ex. Structure logP MH⁺ δ, ppm), selected signals1

3.66 727 2.07 (s, 3H), 2.88 (s, 3H), 3.45 (br s, 3H), 6.35 (s, 2H), 7.29(bs, 1H), 7.38 (s, 1H), 7.54 (d, 1H), 7.58 (dd, 1H), 8.13 (dd, 1H), 8.45(dd, 1H), 10.24 (s, 1H), 10.46 (s, 1H) 2

3.58 805 2.10 (s, 3H), 3.59 (br s, 3H), 6.34 (s, 2H), 7.34 (s, 1H), 7.58(dd, 1H), 7.68 (br s, 1H), 7.81 (d, 1H), 8.14 (dd, 1H), 8.47 (dd, 1H),9.24 (bs, 1H), 10.08 (s, 1H), 10.18 (s, 1H) 3

2.73 (acidic) 613 3.11 (br s, 3H, OMe), 8.95 (s, NH), 9.95 (s, NH),10.02 (s, NH) 4

2.41 (acidic) 604 3.57 (br s, 3H, OMe), 8.99 (s, NH), 10.08 (s, NH),10.29 (s, NH) 5

2.96 (acidic) 627 2.93 (s, 3H, NMe), 3.52 (br s, 3H, OMe), 10.05 (s,NH). 10.29 (s, NH) 6

2.63 (acidic) 618 2.93 (s, 3H, NMe), 3.59 (br s, 3H, OMe), 10.29 (s,NH), 10.40 (s, NH) 7

3.39 (acidic) 641 2.73; 2.82; 2.92 (s, 3H, NMe), 3.42; 3.62 (brs, 3H,OMe) 8

2.97 (acidic) 632 2.76; 2.82; 2.91 (s, 3H, NMe), 3.42; 3.61 (br s, 3H,OMe) 9

4.54 853 2.85 (s, 3H), 3.43; 3.60 (br s, 3H), 10.31 (s, NH), 10.43 (s,NH), 10

4.35 761 2.86 (s, 3H), 3.44; 3.66 (br s, 3H), 10.35 (s, NH), 10.47 (s,NH) 11

3.55 693 2.86 (s, 3H), 3.44; 3.71 (br s, 3H), 10.48 (s, NH), 10.58 (s,NH) 12

3.57 737 2.87 (s, 3H), 3.45; 3.71 (br s, 3H), 10.49 (s, NH), 10.58 (s,NH) 13

4.32 793 2.86 (s, 3H), 3.45; 3.71 (br s, 3H), 10.24 (s, NH), 10.46 (s,NH) 14

4.30 815 2.86 (s, 3H), 3.45; 3.62 (br s, 3H), 10.51 (s, NH), 10.58 (s,NH) 15

3.82 721 2.86 (s, 3H), 3.45; 3.62 (br s, 3H), 10.51 (s, NH), 10.58 (s,NH) 16

3.26 718 2.87 (s, 3H), 3.46; 3.65 (br s, 3H), 10.49 (s, NH), 10.55 (s,NH) 17

3.01 717 2.87 (s, 3H), 3.44; 3.64 (br s, 3H), 10.16 (s, NH), 10.39 (s,NH) 18

4.32 781 CD₃CN: 2.99 (s, 3H), 3.46; 3.66 (br s, 3H), 9.02 (s, NH) 19

3.11 706 2.86 (s, 3H), 3.47; 3.62 (br s, 3H), 10.47 (s, NH), 10.57 (s,NH) 20

3.07 670 CD₃CN: 3.04 (s, 3H), 3.48; 3.66 (br s, 3H), 8.76 (s, NH), 9.06(s, NH) 21

2.51 662 2.87 (s, 3H), 3.45; 3.64 (br s, 3H), 10.47 (s, NH), 10.56 (s,NH) 22

2.53 (acidic) 644 2.88 (s, 3H, NMe), 3.50 (br s, 3H, OMe), 10.45 (s,NH), 10.55 (s, NH) 23

3.14 668 2.87 (s, 3H), 3.58 (s, 3H) 24

2.53 614 2.87 (s, 3H), 3.58 (s, 3H) 25

3.32 697 2.87 (s, 3H), 3.45; 3.63 (br s, 3H), 10.54 (s, NH), 10.57 (s,NH) 26

2.49 609 2.88 (s, 3H), 3.47; 3.63 (br s, 3H), 10.22 (s, NH), 10.45 (s,NH) 27

2.58 653 2.88 (s, 3H), 3.48; 3.62 (br s, 3H), 10.21 (s, NH), 10.45 (s,NH) 28

2.27 629 2.87 (s, 3H), 3.47; 3.64 (br s, 3H), 10.52 (s, NH), 10.57 (s,NH) 29

2.62 617 2.87 (s, 3H), 3.46; 3.65 (br s, 3H), 10.43 (s, NH), 10.54 (s,NH) 30

2.94 626 2.88 (s, 3H), 3.44; 3.65 (br s, 3H), 10.19 (s, NH), 10.44 (s,NH) 31

2.94 648 2.87 (s, 3H), 3.44; 3.64 (br s, 3H), 10.50 (s, NH), 10.56 (s,NH) 32

2.81 718 2.87 (s, 3H), 3.45; 3.65 (br s, 3H), 10.16 (s, NH), 10.42 (s,NH) 33

2.61 626 CD₃CN: 3.04 (s, 3H), 3.47; 3.65 (br s, 3H), 8.74 (s, NH), 9.03(s, NH) 34

2.61 646 CD₃CN: 2.97 (s, 3H), 3.49; 3.65 (br s, 3H), 8.82 (s, NH), 9.03(s, NH) 35

3.14 718 2.87 (s, 3H), 3.44; 3.64 (br s, 3H), 10.16 (s, NH), 10.40 (s,NH) 36

3.10 713 2.86 (s, 3H), 3.47; 3.64 (br s, 3H), 10.47 (s, NH), 10.40 (s,NH) 37

2.18 598 2.88 (s, 3H), 3.61 (s, 3H) 38

2.02 584 3.61 (s, 3H) 39

2.71 612 3.60 (s, 3H) 40

2.98 628 3.59 (s, 3H) 41

3.49 682 3.60 (s, 3H) 42

2.90 677 2.86 (s, 3H), 3.43; 3.62 (br s, 3H), 10.49 (s, NH), 10.54 (s,NH) 43

2.92 647 2.87 (s, 3H), 3.46; 3.64 (br s, 3H), 10.53 (s, NH), 10.57 (s,NH) 44

3.05 661 2.91 (s, 3H), 3.44; 3.65 (br s, 3H), 10.17 (s, NH), 10.43 (s,NH) 45

2.15 600 2.87 (s, 3H), 3.47; 3.64 (br s, 3H), 10.46 (s, NH), 10.55 (s,NH) 46

2.25 609 2.88 (s, 3H), 3.40; 3.64 (br s, 3H), 10.21 (s, NH), 10.45 (s,NH) 47

2.30 617 CD₃CN: 3.03 (s, 3H), 3.50; 3.65 (br s, 3H), 8.88 (s, NH), 9.35(s, NH) 48

3.08 693 2.86 (s, 3H), 3.47; 3.65 (br s, 3H), 10.18 (s, NH), 10.45 (s,NH) 49

3.26 785 2.86 (s, 3H), 3.47; 3.65 (br s, 3H), 10.15 (s, NH), 10.42 (s,NH) 50

2.91 659 2.88 (s, 3H), 3.44; 3.64 (br s, 3H), 10.19 (s, NH), 10.43 (s,NH) 51

3.15 719 2.87 (s, 3H), 3.45; 3.64 (br s, 3H), 10.20 (s, NH), 10.43 (s,NH) 52

3.32 677 2.88 (s, 3H), 3.45; 3.65 (br s, 3H), 10.24 (s, NH), 10.46 (s,NH) 53

3.40 721 2.88 (s, 3H), 3.45; 3.64 (br s, 3H), 10.23 (s, NH), 10.46 (s,NH) 54

3.41 713 3.61 (bs, 3H) 55

2.69 617 3.49 (br, 3H OCH3); 2.76 (s, 3H CH3); 7.95 (s, NH); 7.77 (s,NH) 56

2.97 617 3.57 (br, 3H OCH3); 2.84 (s, 3H CH3); 7.67-7.77 (d, NH);7.79-7.95 (d, NH) 57

3.34 627 3.34 (br, 3H OCH3); 2.9 (s, 3H CH3); 7.49-7.5 (d, NH); 7.54-7.57 (d, NH) 58

2.79 604 3.52 (br, 3H OCH3); 7.54-7.56 (d, NH); 7.75 (s, NH); 7.94 (s,NH) 59

2.73 618 10.57 (s, NH), 10.42 (s, NH), 3.64 and 3.46 (br s, 3H), 2.90(s, 3H) 60

3.17 661 61

3.55 711 10.57 (s, NH), 10.44 (s, NH), 3.64 and 3.46 (br s, 3H), 2.90(s, 3H) 62

2.38 (acidic) 602 1.3 (s, 9H, tBu), 3.6 (br, s, 3H, OMe), 9.3 (br, s,1H, NH), 11.1 (s, br, 1H, NH) 63

2.59 648 10.52 (s, NH) 10.42 (s, NH) 3.64 and 3.46 (br, s, 3H) 2.87 (s,3H) 64

2.09 604/606 NMR in CH₃CN: 9.07 (br, NH), 8.83 (s, NH), 3.70 and 3.46(br, 3H), 3.03 (s, 3H) 65

2.97 665 10.43 (s, NH) 10.12 (s, NH) 3.65 and 3.45 (br, s, 3H) 2.88 (s,3H) 66

3.10 659 10.54 (s, NH) 10.46 (s, NH) 3.63 and 3.44 (br, s, 3H) 2.86 (s,3H) 67

1.90 638 10.56 (s, NH) 10.43 (s, NH) 3.62 and 3.47 (br, s, 3H) 2.87 (s,3H) 68

3.82 739 NMR in CH₃CN: 8.90 (br, NH), 8.70 (s, NH), 3.70 and 3.45 (br,3H), 3.03 (s, 3H) 69

2.71 718 NMR in CH₃CN: 9.04 (br, NH), 8.73 (s, NH), 3.69 and 3.50 (br,3H), 3.04 (s, 3H) 70

2.81 714 NMR in CH₃CN: 9.01 (br, NH), 8.78 (s, NH), 3.65 and 3.52 (br,3H), 3.06 (s, 3H) 71

2.42 646 10.45 (s, NH) 10.15 (s, NH) 3.60 and 3.51 (br, s, 3H) 2.90 (s,3H) 72

2.78 719 10.43 (s, NH) 10.19 (s, NH) 3.60 and 3.50 (br, s, 3H) 2.87 (s,3H) 73

2.97 668 10.55 (s, NH) 10.48 (s, NH) 3.60 and 3.47 (br, s, 3H) 2.87 (s,3H) 74

2.64 701 10.41 (s, NH) 10.19 (s, NH) 3.64 and 3.45 (br, s, 3H) 2.87 (s,3H) 75

2.19 593 10.41 (s, NH) 10.15 (s, NH) 3.66 and 3.48 (br, s, 3H) 2.90 (s,3H) 76

2.77 684 10.55 (s, NH) 10.42 (s, NH) 3.60 and 3.47 (br, s, 3H) 2.87 (s,3H) 77

2.56 717 10.45 (s, NH) 10.20 (s, NH) 3.64 and 3.45 (br, s, 3H) 2.86 (s,3H) 78

2.10 616 NMR in CH₃CN: 9.40 (br, NH), 8.95 (s, NH), 3.65 and 3.50 (br,3H), 3.01 (s, 3H) 79

3.66 732 10.62 (s, NH) 10.35 (s, NH) 3.68 and 3.58 (br, s, 3H) 3.06 (s,3H) 80

2.38 703 NMR in DMF-d₉: 10.34 (s, NH), 10.25 (s, NH), 9.33 (s, NH), 3.51(s, 3H), 2.95 (s, 3H) 81

3.85 82

3.67 83

2.97 620 10.37 (br s, NH), 7.95 (br s, NH), 3.30 (brs, 3H), 2.84 (s, 3H)84

2.79 603 10.22 (br s, NH), 7.94 (br, NH), 3.60 (br, 3H) 85

3.34 627 10.13 (br, NH), 7.5 (br, NH), 3.39 (br, 3H), 2.79 (s, 3H) 86

2.69 620 10.37 (br, NH), 7.94 (br, NH), 3.30 (br, 3H), 2.67 (br, 3H),

APPLICATION EXAMPLES Example 1

Myzus Test (MYZUPE Spray Treatment)

-   Solvent: 78.0 parts by weight of acetone    -   1.5 parts by weight of dimethylformamide-   Emulsifier: 0.5 part by weight of alkylaryl polyglycol ether

An appropriate preparation of active ingredient is prepared by mixing 1part by weight of active ingredient with the stated amounts of solventand emulsifier and diluting the concentrate with emulsifier-containingwater to the desired concentration. Leaf discs of Chinese cabbage(Brassica pekinensis) infested with all stages of the green peach aphid(Myzus persicae) are sprayed with a preparation of active ingredient atthe desired concentration.

After 6 days the activity is determined, in %. Here, 100% means that allof the aphids have been killed; 0% means that no aphids have beenkilled.

In this test, for example, the following compounds from the PreparationExamples exhibit activity of

80% at an application rate of 100 g/ha: Ex.: 39, 65, 77, 81

In this test, for example, the following compounds from the PreparationExamples exhibit activity of

90% at an application rate of 100 g/ha: Ex.: 11, 20, 21, 32, 47, 54, 61,78

In this test, for example, the following compounds from the PreparationExamples exhibit activity of

100% at an application rate of 100 g/ha: Ex.: 1, 3, 4, 5, 6, 7, 8, 12,16, 17, 22, 23, 25, 26, 27, 28, 29, 30, 31, 33, 34, 35, 36, 37, 38, 41,42, 45, 46, 48, 49, 50, 51, 52, 53 60, 63, 66, 68, 69, 72, 73, 74, 75,79, 82, 83, 84, 85, 86

Example 2

Phaedon Test (PHAECO Spray Treatment)

-   Solvent: 78.0 parts by weight of acetone    -   1.5 parts by weight of dimethylformamide-   Emulsifier: 0.5 part by weight of alkylaryl polyglycol ether

An appropriate preparation of active ingredient is prepared by mixing 1part by weight of active ingredient with the stated amounts of solventand emulsifier and diluting the concentrate with emulsifier-containingwater to the desired concentration. Leaf discs of Chinese cabbage(Brassica pekinensis) are sprayed with a preparation of activeingredient at the desired concentration and, after drying, are populatedwith larvae of the mustard beetle (Phaedon cochleariae).

After 7 days, the activity is determined, in %. Here, 100% means thatall the beetle larvae have been killed; 0% means that no beetle larvaehave been killed.

In this test, for example, the following compounds from the PreparationExamples exhibit activity of 100% at an application rate of 100 g/ha:

Ex.: 1, 2, 3, 4, 5, 6, 7, 8, 11, 12, 13, 14, 16, 17, 19, 20, 22, 23, 25,26, 27, 28, 29, 30, 31, 32, 33, 34, 35, 36, 37, 38, 41, 42, 45, 46, 47,48, 49, 50, 51, 52, 53, 54, 59, 60, 61, 63, 66, 68, 69, 72, 73, 74, 75,79, 81, 82, 83, 84, 85, 86

Example 3

Spodoptera frugiperda test (SPODFR Spray Treatment)

-   Solvent: 78.0 parts by weight of acetone    -   1.5 parts by weight of dimethylformamide-   Emulsifier: 0.5 part by weight of alkylaryl polyglycol ether

An appropriate preparation of active ingredient is prepared by mixing 1part by weight of active ingredient with the stated amounts of solventand emulsifier and diluting the concentrate with emulsifier-containingwater to the desired concentration. Leaf discs of maize (Zea mays) aresprayed with a preparation of active ingredient at the desiredconcentration and, after drying, are populated with caterpillars of thearmy worm (Spodoptera frugiperda).

After 7 days, the activity is determined, in %. Here, 100% means thatall the caterpillars have been killed; 0% means that no caterpillar hasbeen killed.

In this test, for example, the following compound from the PreparationExamples exhibits activity of

83% at an application rate of 100 g/ha: Ex.: 77

In this test, for example, the following compound from the PreparationExamples exhibits activity of

100% at an application rate of 100 g/ha:

Ex.: 1, 2, 3, 4, 5, 6, 7, 8, 11, 12, 13, 14, 15, 16, 17, 19, 20, 21, 23,25, 26, 27, 28, 29, 30, 31, 32, 33, 34, 35, 36, 37, 38, 41, 42, 45, 46,47, 48, 49, 50, 51, 52, 53, 54, 59, 60, 61, 62, 63, 65, 66, 68, 69, 72,73, 74, 75, 79, 81, 82, 83, 84, 85, 86

Example 4

Tetranychus Test, OP-Resistant (TETRUR Spray Treatment)

-   Solvent: 78.0 parts by weight of acetone    -   1.5 parts by weight of dimethylformamide-   Emulsifier: 0.5 part by weight of alkylaryl polyglycol ether

An appropriate preparation of active ingredient is prepared by mixing 1part by weight of active ingredient with the stated amounts of solventand emulsifier and diluting the concentrate with emulsifier-containingwater to the desired concentration. Leaf discs of bean (Phaseolusvulgaris) infested with all stages of the greenhouse red spidermite(Tetranychus urticae) are sprayed with a preparation of activeingredient at the desired concentration. After 6 days the activity isdetermined, in %. Here, 100% means that all of the mites have beenkilled; 0% means that no mites have been killed.

In this test, for example, the following compound from the PreparationExamples exhibits activity of 90% at an application rate of 100 g/ha: 83

In this test, for example, the following compound from the PreparationExamples exhibits activity of 100% at an application rate of 100 g/ha:59

In this test, for example, the following compound from the PreparationExamples exhibits activity of 100% at an application rate of 500 g/ha:67.

Analytical Methods

The log P values reported in the table above and in the PreparationExamples were determined in accordance with EEC Directive 79/831 AnnexV.A8 by HPLC (High Performance Liquid Chromatography) on reversed-phasecolumns (C 18), with the following methods:

^([a]) The determination is made in the acid range at pH 2.3 with 0.1%aqueous phosphoric acid and acetonenitrile as eluents; linear gradientfrom 10% acetonitrile to 95% acetonitrile.

^([b]) The determination is made by LC-MS in the acid range at pH 2.7with 0.1% aqueous formic acid and acetonitrile (containing 0.1% formicacid) as eluents; linear gradient from 10% acetonitrile to 95%acetoneitrile.

Calibration took place with unbranched alkan-2-ones (having 3 to 16carbon atoms) of known log P values (log P values determined from theretention times, by linear interpolation between two successivealkanones).

The lambda-maX values were determined on the basis of the UV spectrafrom 200 nm to 400 nm in the maxima of the chromatographic signals.

The MH⁺ signals were determined using an Agilent MSD system with ESI andpositive or negative ionization.

The NMR spectra were

a) determined with a Bruker Avance 400 equipped with a flow sample head(60 μl volume). Solvents used were CD₃CN or d₆-DMSO, andtetramethylsilane (0.00 ppm) was used as reference.

b) determined with a Bruker Avance II 600. Solvents used were CD₃CN ord₆-DMSO, with tetramethylsilane (0.00 ppm) used as reference.

The splitting of the signals was described as follows: s (singlet), d(doublet), t (triplet), q (quartet), quin (quintet), m (multiplet).

1. An anthranilic acid derivative of general formula (I)

in which R¹ is hydrogen, amino, or hydroxyl or is C₁-C₆-alkyl,C₂-C₆-alkenyl, C₂-C₆-alkynyl or C₃-C₆-cycloalkyl, each of which isoptionally substituted one or more times by identical or differentsubstituents, the substituents being selectable independently of oneanother from halogen, cyano, nitro, hydroxyl, C₁-C₄-alkoxy,C₁-C₄-alkylthio, C₁-C₄-alkylsulphinyl, C₁-C₄-alkylsulphonyl,(C₁-C₄-alkoxy)carbonyl, C₁-C₄-alkylamino, di(C₁-C₄-alkyl)amino,C₃-C₆-cycloalkylamino or (C₁-C₄-alkyl)C₃-C₆-cycloalkylamino, R², R³independently of one another are hydrogen, C₂-C₆-alkoxycarbonyl,C₂-C₆-alkylcarbonyl, C₂-C₆-alkylaminocarbonyl, orC₂-C₆-dialkylaminocarbonyl or are C₁-C₆-alkyl, C₁-C₆-alkoxy,C₂-C₆-alkenyl, C₂-C₆-alkynyl or C₃-C₆-cycloalkyl, each of which isoptionally substituted one or more times by identical or differentsubstituents, the substituents being selectable independently of oneanother from halogen, cyano, nitro, hydroxyl, C₁-C₆-alkyl,C₃-C₆-cycloalkyl, C₁-C₄-alkoxy, C₁-C₄-haloalkoxy, C₁-C₄-alkylthio,C₁-C₄-alkylsulphinyl, C₁-C₄-alkylsulphonyl, C₁-C₄-alkylsulphimino,C₁-C₄-alkylsulphimino-C₁-C₄-alkyl,C₁-C₄-alkylsulphimino-C₂-C₅-alkylcarbonyl, C₁-C₄-alkylsulphoximino,C₁-C₄-alkylsulphoximino-C₁-C₄-alkyl,C₁-C₄-alkylsulphoximino-C₂-C₅-alkylcarbonyl, C₂-C₆-alkoxycarbonyl,C₂-C₆-alkylcarbonyl or C₃-C₆-trialkylsilyl, or R², R³ independently ofone another are a phenyl ring or a 5- or 6-membered unsaturated,partially saturated or saturated heterocycle, the phenyl ring orheterocycle being optionally substituted one or more times by identicalor different substituents, and the substituents being selectableindependently of one another from hydrogen, C₁-C₆-alkyl, C₂-C₆-alkenyl,C₂-C₆-alkynyl, C₃-C₆-cycloalkyl, C₁-C₆-haloalkyl, C₂-C₆-haloalkenyl,C₂-C₆-haloalkynyl, C₃-C₆-halocycloalkyl, halogen, CN, (C═O)OH, (C═O)NH₂,NO₂, OH, C₁-C₄-alkoxy, C₁-C₄-haloalkoxy, C₁-C₄-alkylthio,C₁-C₄-alkylsulphinyl, C₁-C₄-alkylsulphonyl, C₁-C₄-haloalkylthio,C₁-C₄-haloalkylsulphinyl, C₁-C₄-haloalkylsulphonyl, C₁-C₄-alkylamino,di(C₁-C₄-alkyl)amino, C₃-C₆-cycloalkylamino, (C₁-C₆-alkyl)carbonyl,(C₁-C₆-alkoxy)carbonyl, (C₁-C₆-alkyl)aminocarbonyl,di(C₁-C₄-alkyl)aminocarbonyl, tri(C₁-C₂)alkylsilyl, or(C₁-C₄-alkyl)(C₁-C₄-alkoxy)imino, or R² and R³ are joined to one anothervia two to six carbon atoms and form a ring which optionallyadditionally contains a nitrogen, sulphur or oxygen atom and mayoptionally be substituted one to four times by C₁-C₂-alkyl,C₁-C₂-haloalkyl, halogen, cyano, amino, C₁-C₂-alkoxy orC₁-C₂-haloalkoxy, R⁴ is a group selected from —C(═S)—R⁸, —C(═)—R⁸,—C(═O)—OR⁹, —C(═S)—OR⁹, —C(═O)—SR¹⁰, —C(═S)—SR¹⁰, —C(═O)—NR¹¹R¹²,—C(═S)—NR¹¹R¹², —S(O)₂—R¹³, or —S(O)₂—NR¹⁴R¹⁵, or R³, R⁴ together are═CR¹⁶ if R² and R³ are not joined to one another via two to six carbonatoms and do not form a ring, R⁵ is hydrogen, halogen, cyano, nitro,C₁-C₄-alkyl, C₁-C₄-haloalkyl, C₂-C₆-alkenyl, C₂-C₆-haloalkenyl,C₂-C₆-alkynyl, C₁-C₄-alkoxy, C₁-C₄-haloalkoxy, SF₅, C₁-C₄-alkylthio,C₁-C₄-alkylsulphinyl, C₁-C₄-alkylsulphonyl, C₁-C₄-haloalkylthio,alkylsulphinyl, C₁-C₄-haloalkylsulphonyl, C₁-C₄-alkylamino,di(C₁-C₄-alkyl)amino, C₃-C₆-cycloalkylamino, (C₁-C₄-alkoxy)imino,(C₁-C₄-alkyl)(C₁-C₄-alkoxy)imino, (C₁-C₄-haloalkyl)(C₁-C₄-alkoxy)imino,or C₃-C₆-trialkylsilyl, or two radicals R⁵ form, via adjacent carbonatoms, a ring which is —(CH₂)₃—, —(CH₂)₄—, —(CH₂)₅—, —(CH═CH—)₂—,—OCH₂O—, —O(CH₂)₂O—, —OCF₂O—, —(CF₂)₂O—, —O(CF₂)₂O—, —(CH═CH—CH═N)—, or—(CH═CH—N═CH)—, or two radicals R⁵, form via adjacent carbon atoms thefused rings below, which are optionally substituted one or more times byidentical or different substituents, the substituents being selectableindependently of one another from hydrogen, cyano, C₁-C₆-alkyl,C₃-C₆-cycloalkyl, C₁-C₆-haloalkyl, C₃-C₆-halocycloalkyl, halogen,C₁-C₆-alkoxy, C₁-C₄-alkylthio(C₁-C₆-alkyl),C₁-C₄-alkylsulphinyl(C₁-C₆-alkyl), C₁-C₄-alkylsulphonyl(C₁-C₆-alkyl),C₁-C₄-alkylamino, di(C₁-C₄-alkyl)amino or C₃-C₆-cycloalkylamino,

n is 0 to 3, is O or S, R⁶ is C₁-C₆-alkyl, C₃-C₆-cycloalkyl,C₁-C₆-haloalkyl, C₁-C₆-halocycloalkyl, C₂-C₆-alkenyl, C₂-C₆-haloalkenyl,C₂-C₆-alkynyl, C₂-C₆-haloalkynyl, C₁-C₄-alkoxy, C₁-C₄-haloalkoxy,C₁-C₄-alkylthio, C₁-C₄-alkylsulphinyl, C₁-C₄-alkylsulphonyl,C₁-C₄-haloalkylthio, C₁-C₄-haloalkylsulphinyl, haloalkylsulphonyl,halogen, cyano, nitro, or C₃-C₆-trialkylsilyl, Q_(X) is an aromatic orheteroaromatic 5- to 6-membered ring which is optionally substituted oneor more times by identical or different substituents R⁷ and which maycontain 1-3 heteroatoms from the series N, S or O, A is optionallysingly or multiply substituted —(C₁-C₆-alkylene)-, —(C₁-C₆-alkenylene)-,—(C₁-C₆-alkynylene)-, —R¹⁷—(C₃-C₆-cycloalkyl)-R¹⁷—, —R¹⁷—O—R¹⁷—,—R¹⁷—S—R¹⁷—, —R¹⁷—S(═O)—R¹⁷—, —R¹⁷—S(═O)₂—R¹⁷—, —R¹⁷—NH—(C₁-C₆-alkyl)-,—R¹⁷—N(C₁-C₆-alkyl)-R¹⁷—, —R¹⁷—C═NO(C₁-C₆-alkyl), —CH[CO₂(C₁-C₆-alkyl)-,—R¹⁷—C(═O)—R¹⁷, —R¹⁷—C(═O)NH—R¹⁷, R¹⁷—C(═O)N(C₁-C₆-alkyl)-R¹⁷,—R¹⁷—C(═O)NHNH—R¹⁷—, —R¹⁷—C(═O)N(C₁-C₆-alkyl)-NH—R¹⁷—,—R¹⁷—C(═O)NHN(C₁-C₆-alkyl)-R¹⁷, —R¹⁷—O(C═O)—R¹⁷, —R¹⁷—O(C═O)NH—R¹⁷,—R¹⁷—O(C═O)N(C₁-C₆-alkyl)-R¹⁷, —R¹⁷—S(═O)₂NH—R¹⁷,—R¹⁷—S(═O)₂N(C₁-C₆-alkyl)-R¹⁷, —R¹⁷—S(C═O)—R¹⁷, —R¹⁷—S(C═O)NH—R¹⁷,—R¹⁷—S(C═O)N(C₁-C₆-alkyl)-R¹⁷, —R¹⁷—NHNH—R¹⁷, —R¹⁷—NHN(C₁-C₆-alkyl)-R¹⁷,—R¹⁷—N(C₁-C₆-alkyl)-NH—R¹⁷, —R¹⁷—N(C₁-C₆-alkyl)-N(C₁-C₆-alkyl)-R¹⁷,—R¹⁷—N═CH—O—R¹⁷, —R¹⁷—NH(C═O)O—R¹⁷, —R¹⁷—N(C₁-C₆-alkyl)-(C═O)O—R¹⁷,—R¹⁷—NH(C═O)NH—R¹⁷, —R¹⁷—NH(C═S)NH—R¹⁷, —R¹⁷—NHS(═O)₂—R¹⁷, or—R¹⁷—N(C₁-C₆-alkyl)S(═O)₂—R¹⁷, the substituents being selectableindependently of one another from halogen, cyano, nitro, hydroxyl,C₁-C₆-alkyl, C₁-C₆-alkoxy, or halo-C₁-C₆-alkyl, where—(C₃-C₆-cycloalkyl)- in the ring may optionally contain 1 to 2heteroatoms selected from the series N, S or O, R¹⁷ is linear orbranched —(C₁-C₆-alkylene)- or is a direct bond, or two or more radicalsR¹⁷ independently of one another are linear or branched—(C₁-C₆-alkylene)- or are a direct bond, Q_(Y) is a 5- or 6-membered,partially saturated or saturated heterocyclic or heteroaromatic ring oran aromatic 8-, 9- or 10-membered fused heterobicyclic ring system or isphenyl, the ring or ring system being optionally substituted one or moretimes by identical or different substituents, and the substituents beingselectable independently of one another from hydrogen, C₁-C₆-alkyl,C₂-C₆-alkenyl, C₂-C₆-alkynyl, C₃-C₆-cycloalkyl, C₁-C₆-haloalkyl,C₂-C₆-haloalkenyl, C₂-C₆-haloalkynyl, C₃-C₆-halocycloalkyl, halogen, CN,CO₂H, CO₂NH₂, NO₂, OH, C₁-C₄-alkoxy, C₁-C₄-haloalkoxy, C₁-C₄-alkylthio,C₁-C₄-alkylsulphinyl, C₁-C₄-alkylsulphonyl, C₁-C₄-haloalkylthio,C₁-C₄-haloalkylsulphinyl, C₁-C₄-haloalkylsulphonyl, C₁-C₄-alkylamino,di(C₁-C₄-alkyl)amino, C₃-C₆-cycloalkylamino, (C₁-C₆-alkyl)carbonyl,(C₁-C₆-alkoxy)carbonyl, (C₁-C₆-alkyl)aminocarbonyl,di(C₁-C₄-alkyl)aminocarbonyl, tri(C₁-C₂)alkylsilyl, or(C₁-C₄-alkyl)(C₁-C₄-alkoxy)imino, or the substituents being selectableindependently of one another from phenyl or a 5- or 6-memberedheteroaromatic ring, where phenyl or the ring may optionally besubstituted one or more times by identical or different C₁-C₆-alkyl,C₂-C₆-alkenyl, C₂-C₆-alkynyl, C₃-C₆-cycloalkyl, C₁-C₆-haloalkyl,C₂-C₆-haloalkenyl, C₂-C₆-haloalkynyl, C₃-C₆-halocycloalkyl, halogen, CN,NO₂, OH, C₁-C₄-alkoxy, or C₁-C₄-haloalkoxy substituents, R⁷ is hydrogen,C₁-C₆-alkyl, C₂-C₆-alkenyl, C₂-C₆-alkynyl, C₃-C₆-cycloalkyl,C₁-C₆-haloalkyl, C₂-C₆-haloalkenyl, C₃-C₆-cycloalkoxy, or

R independently at each occurrence is hydrogen, C₁-C₆-alkyl,C₃-C₆-cycloalkyl, C₁-C₆-haloalkyl, halogen, cyano, nitro, C₁-C₄-alkoxy,C₁-C₄-haloalkoxy, C₁-C₄-haloalkylthio, C₁-C₄-haloalkylsulphonyl or(C₁-C₄-alkyl)C₁-C₄-alkoxyimino, m is 0 to 4, Z is N, CH, CF, CCl, CBr orCI, R⁸ is hydrogen or is C₁-C₆-alkyl, C₂-C₆-alkenyl, C₂-C₆-alkynyl,C₃-C₁₂-cycloalkyl, C₃-C₁₂-cycloalkyl-C₁-C₆-alkyl or C₄-C₁₂-bicycloalkyl,each of which is optionally substituted one or more times by identicalor different substituents, the substituents being selectableindependently of one another from halogen, cyano, nitro, hydroxyl,C₁-C₆-alkyl, C₃-C₆-cycloalkyl, C₁-C₄-alkoxy, C₁-C₄-haloalkoxy,C₁-C₄-alkylthio, C₁-C₄-alkylsulphinyl, C₁-C₄-alkylsulphonyl,C₁-C₄-alkylsulphimino, C₁-C₄-alkylsulphimino-C₁-C₄-alkyl,C₁-C₄-alkylsulphimino-C₂-C₅-alkylcarbonyl, C₁-C₄-alkylsulphoximino,C₁-C₄-alkylsulphoximino-C₁-C₄-alkyl,C₁-C₄-alkylsulphoximino-C₂-C₅-alkylcarbonyl, C₂-C₆-alkoxycarbonyl,C₂-C₆-alkylcarbonyl, C₃-C₆-trialkylsilyl, amino, C₁-C₄-alkylamino,di(C₁-C₄-alkyl)amino, C₃-C₆-cycloalkylamino, a phenyl ring or a 3- to6-membered unsaturated, partially saturated or saturated heterocycle,the phenyl ring or heterocycle being optionally substituted one or moretimes by identical or different substituents, and the substituents beingselectable independently of one another from hydrogen, C₁-C₆-alkyl,C₂-C₆-alkenyl, C₂-C₆-alkynyl, C₃-C₆-cycloalkyl, C₁-C₆-haloalkyl,C₂-C₆-haloalkenyl, C₂-C₆-haloalkynyl, C₃-C₆-halocycloalkyl, halogen, CN,(C═O)OH, CONH₂, NO₂, OH, C₁-C₄-alkoxy, C₁-C₄-haloalkoxy,C₁-C₄-alkylthio, C₁-C₄-alkylsulphinyl, C₁-C₄-alkylsulphonyl,C₁-C₄-haloalkylthio, C₁-C₄-haloalkylsulphinyl, C₁-C₄-haloalkylsulphonyl,C₁-C₄-alkylamino, di(C₁-C₄-alkyl)amino, C₃-C₆-cycloalkylamino,(C₁-C₆-alkyl)carbonyl, (C₁-C₆-alkoxy)carbonyl,(C₁-C₆-alkyl)aminocarbonyl, di(C₁-C₄-alkyl)aminocarbonyl,tri(C₁-C₂)alkylsilyl, or (C₁-C₄-alkyl)(C₁-C₄-alkoxy)imino, or R⁸ is aphenyl ring or a 3- to 6-membered unsaturated, partially saturated orsaturated heterocycle, the heteroatoms being selected from the series N,S or O, where the phenyl ring or heterocycle is optionally substitutedone or more times by identical or different substituents, and where thesubstituents are selectable independently of one another from hydrogen,C₁-C₆-alkyl, C₂-C₆-alkenyl, C₂-C₆-alkynyl, C₃-C₆-cycloalkyl,C₁-C₆-haloalkyl, C₂-C₆-haloalkenyl, C₂-C₆-haloalkynyl,C₃-C₆-halocycloalkyl, halogen, CN, (C═O)OH, CONH₂, NO₂, OH,C₁-C₄-alkoxy, C₁-C₄-haloalkoxy, C₁-C₄-alkylthio, C₁-C₄-alkylsulphinyl,C₁-C₄-alkylsulphonyl, C₁-C₄-haloalkylthio, C₁-C₄-haloalkylsulphinyl,C₁-C₄-haloalkylsulphonyl, C₁-C₄-alkylamino, di(C₁-C₄-alkyl)amino,C₃-C₆-cycloalkylamino, (C₁-C₆-alkyl)carbonyl, (C₁-C₆-alkoxy)carbonyl,(C₁-C₆-alkyl)aminocarbonyl, di(C₁-C₄-alkyl)amino carbonyl,tri(C₁-C₂)alkylsilyl, or (C₁-C₄-alkyl)(C₁-C₄-alkoxy)imino, R⁹, R¹⁰, R¹³,R¹⁴ and R¹⁵ independently of one another are C₁-C₆-alkyl, C₂-C₆-alkenyl,C₂-C₆-alkynyl, C₃-C₁₂-cycloalkyl, C₃-C₁₂-cycloalkyl-C₁-C₆-alkyl orC₄-C₁₂-bicycloalkyl, each of which is optionally substituted one or moretimes by identical or different substituents, the substituents beingselectable independently of one another from halogen, cyano, nitro,hydroxyl, C₁-C₆-alkyl, C₃-C₆-cycloalkyl, C₁-C₄-alkoxy, C₁-C₄-haloalkoxy,C₁-C₄-alkylthio, C₁-C₄-alkylsulphinyl, C₁-C₄-alkylsulphonyl,C₁-C₄-alkylsulphimino, C₁C₄-alkylsulphimino-C₁-C₄-alkyl,C₁-C₄-alkylsulphimino-C₂-C₅-alkylcarbonyl, C₁-C₄-alkylsulphoximino,C₁-C₄-alkylsulphoximino-C₁-C₄-alkyl,C₁-C₄-alkylsulphoximino-C₂-C₅-alkylcarbonyl, C₂-C₆-alkoxycarbonyl,C₂-C₆-alkylcarbonyl, C₃-C₆-trialkylsilyl, amino, C₁-C₄-alkylamino,di(C₁-C₄-alkyl)amino, C₃-C₆-cycloalkylamino, a phenyl ring or a 3- or6-membered unsaturated, partially saturated or saturated heterocycle,the phenyl ring or heterocycle being optionally substituted one or moretimes by identical or different substituents, and the substituents beingselectable independently of one another from hydrogen, C₁-C₆-alkyl,C₂-C₆-alkenyl, C₂-C₆-alkynyl, C₃-C₆-cycloalkyl, C₁-C₆-haloalkyl,C₂-C₆-haloalkenyl, C₂-C₆-haloalkynyl, C₃-C₆-halocycloalkyl, halogen, CN,(C═O)OH, CONH₂, NO₂, OH, C₁-C₄-alkoxy, C₁-C₄-haloalkoxy,C₁-C₄-alkylthio, C₁-C₄-alkylsulphinyl, C₁-C₄-alkylsulphonyl,C₁-C₄-haloalkylthio, C₁-C₄-haloalkylsulphinyl, C₁-C₄-haloalkylsulphonyl,C₁-C₄-alkylamino, di(C₁-C₄-alkyl)amino, C₃-C₆-cycloalkylamino,(C₁-C₆-alkyl)carbonyl, (C₁-C₆-alkoxy)carbonyl,(C₁-C₆-alkyl)aminocarbonyl, di(C₁-C₄-alkyl)aminocarbonyl,tri(C₁-C₂)alkylsilyl or (C₁-C₄-alkyl)(C₁-C₄-alkoxy)imino, or R⁹, R¹⁰,R¹³, R¹⁴ and R¹⁵ independently of one another are a phenyl ring or are a3- to 6-membered unsaturated, partially saturated or saturatedheterocycle, the heteroatoms being selected from the series N, S or O,the phenyl ring or heterocycle being optionally substituted one or moretimes by identical or different substituents, and the substituents beingselectable independently of one another from hydrogen, C₁-C₆-alkyl,C₂-C₆-alkenyl, C₂-C₆-alkynyl, C₃-C₆-cycloalkyl, C₁-C₆-haloalkyl,C₂-C₆-haloalkenyl, C₂-C₆-haloalkynyl, C₃-C₆-halocycloalkyl, halogen, CN,(C═O)OH, CONH₂, NO₂, OH, C₁-C₄-alkoxy, C₁-C₄-haloalkoxy,C₁-C₄-alkylthio, C₁-C₄-alkylsulphinyl, C₁-C₄-alkylsulphonyl,C₁-C₄-haloalkylthio, C₁-C₄-haloalkylsulphinyl, C₁-C₄-haloalkylsulphonyl,C₁-C₄-alkylamino, di(C₁-C₄-alkyl)amino, C₃-C₆-cycloalkylamino,(C₁-C₆-alkyl)carbonyl, (C₁-C₆-alkoxy)carbonyl,(C₁-C₆-alkyl)aminocarbonyl, di(C₁-C₄-alkylaminocarbonyl,tri(C₁-C₂)alkylsilyl, or (C₁-C₄-alkyl)(C₁-C₄-alkoxy)imino, R¹¹, R¹²independently of one another are hydrogen or are R⁹, R¹⁶ is a phenylring or is a 5- or 6-membered heteroaromatic ring, the heteroatoms beingselected from the series N, S or O, the ring being optionallysubstituted one or more times by identical or different substituents,and the substituents being selectable independently of one another fromhydrogen, C₁-C₆-alkyl, C₂-C₆-alkenyl, C₂-C₆-alkynyl, C₃-C₆-cycloalkyl,C₁-C₆-haloalkyl, C₂-C₆-haloalkenyl, C₂-C₆-haloalkynyl,C₃-C₆-halocycloalkyl, halogen, CN, (C═O)OH, CONH₂, NO₂, OH,C₁-C₄-alkoxy, C₁-C₄-haloalkoxy, C₁-C₄-alkylthio, C₁-C₄-alkylsulphinyl,C₁-C₄-alkylsulphonyl, C₁-C₄-haloalkylthio, C₁-C₄-haloalkylsulphinyl,C₁-C₄-haloalkylsulphonyl, C₁-C₄-alkylamino, di(C₁-C₄-alkyl)amino,C₃-C₆-cycloalkylamino, (C₁-C₆-alkyl)carbonyl, (C₁-C₆-alkoxy)carbonyl,(C₁-C₆-alkyl)aminocarbonyl, di(C₁-C₄-alkyl)aminocarbonyl,tri(C₁-C₂)alkylsilyl or (C₁-C₄-alkyl)(C₁-C₄-alkoxy)imino, and N-oxidesand salts thereof.
 2. An anthranilic acid derivative of general formula(I) according to claim 1, in which R¹ is hydrogen, C₁-C₆-alkyl,C₂-C₆-alkenyl, C₂-C₆-alkynyl, C₃-C₆-cycloalkyl, cyano(C₁-C₆-alkyl),C₁-C₆-haloalkyl, C₂-C₆-haloalkenyl, C₂-C₆-haloalkynyl,C₁-C₄-alkoxy-C₁-C₄-alkyl, C₁-C₄-alkylthio-C₁-C₄-alkyl,C₁-C₄-alkylsulphinyl-C₁-C₄-alkyl, or C₁-C₄-alkylsulphonyl-C₁-C₄-alkyl,R², R³ independently of one another are hydrogen or are C₁-C₆-alkyl orC₃-C₆-cycloalkyl optionally substituted one or more times by identicalor different substituents, the substituents being selectableindependently of one another from halogen, cyano, C₂-C₆-alkoxycarbonyl,or C₂-C₆-alkylcarbonyl, R⁴ is —C(═O)—R⁸, 'C(═O)—OR⁹, —C(═O)—SR¹⁰,—C(═O)—NR¹¹R¹², —S(O)₂—R¹³, or —S(O)₂—NR¹⁴R¹⁵, R⁵ is hydrogen,C₁-C₄-alkyl, C₁-C₄-haloalkyl, halogen, cyano, C₁-C₄-alkoxy,C₁-C₄-haloalkoxy, C₁-C₄-alkylthio, or C₁-C₄-haloalkylthio, or twoadjacent radicals R⁵ are —(CH₂)₃—, —(CH₂)₄—, —(CH₂)₅—, —(CH═CH—)₂—,—OCH₂O—, —O(CH₂)₂O—, —OCF₂O—, —(CF₂)₂O—, —O(CF₂)₂O—, —(CH═CH—CH═N)—, or—(CH═CH—N═CH)—, n is 0 to 2, X is O or S, R⁶ is C₁-C₄-alkyl,C₃-C₆-cycloalkyl, C₁-C₄-haloalkyl, C₁-C₆-halocycloalkyl, C₂-C₆-alkenyl,C₂-C₄-haloalkenyl, C₂-C₄-alkynyl, C₂-C₄-haloalkynyl, C₁-C₄-alkoxy,C₁-C₄-haloalkoxy, C₁-C₄-alkylthio, C₁-C₄-alkylsulphinyl,C₁-C₄-alkylsulphonyl, C₁-C₄-haloalkylthio, C₁-C₄-haloalkylsulphinyl,C₁-C₄-haloalkylsulphonyl, halogen, cyano, nitro, or C₃-C₆-trialkylsilyl,Q_(X) is a heteroaromatic 5-membered ring which is optionallysubstituted one or more times by identical or different substituents R⁷and which may contain 1-3 heteroatoms from the series N, O or S, or is aheteroaromatic 6-membered ring which is optionally substituted one ormore times by identical or different substituents R⁷ and which maycontain 1-3 nitrogen atoms, or is phenyl, A is optionally singly ormultiply substituted —(C₁-C₄-alkylene)-, —(C₁-C₄-alkenylene)-,—(C₁-C₄-alkynylene)-, —R¹⁷—(C₃-C₆-cycloalkyl)-R¹⁷—, —R¹⁷—O—R¹⁷—,—R¹⁷—S—R¹⁷—, —R¹⁷—S(═O)—R¹⁷—, —R¹⁷—S(═O)₂—R¹⁷—, —R¹⁷—NH—(C₁-C₄-alkyl)-,—R¹⁷—N(C₁-C₄-alkyl)-R¹⁷, —R¹⁷—C═NO(C₁-C₄-alkyl), —R¹⁷—C(═O)—R¹⁷,—R¹⁷—C(═S)—R¹⁷, —R¹⁷—C(═O)NH—R¹⁷, R¹⁷—C(═O)N(C₁-C₄-alkyl)-R¹⁷,—R¹⁷—S(═O)₂NH—R¹⁷, —R¹⁷—S(═O)₂N(C₁-C₄-alkyl)-R¹⁷, —R¹⁷—NH(C═O)O—R¹⁷,—R¹⁷—N(C₁-C₄-alkyl)-(C═O)O—R¹⁷, —R¹⁷—NH(C═O)NH—R¹⁷, —R¹⁷—NHS(═O)₂—R¹⁷,or —R¹⁷—N(C₁-C₄-alkyl)S(═O)₂—R¹⁷, the substituents being selectableindependently of one another from halogen, cyano, nitro, hydroxyl,C₁-C₆-alkyl, C₁-C₆-alkoxy, or halo-C₁-C₆-alkyl, R⁷ is C₁-C₆-alkyl or isthe radical

or R⁷ is C₃-C₆-cycloalkoxy, R independently at each occurrence ishydrogen, halogen, cyano, C₁-C₄-alkyl, C₁-C₄-alkoxy, C₁-C₄-haloalkyl,C₁-C₄-haloalkoxy, C₁-C₄-haloalkylsulphonyl, or (C₁-C₄-alkyl)C₁-C-alkoxyimino, m is 1, 2 or 3, R⁸ is hydrogen or singly or multiplyidentically or differently substituted C₁-C₆-alkyl or C₃-C₆-cycloalkyl,the substituents being selectable independently of one another fromhalogen, cyano, a phenyl ring or a 3- or 6-membered unsaturated,partially saturated or saturated heterocycle, the phenyl ring orheterocycle being optionally substituted one or more times by identicalor different substituents, and the substituents being selectableindependently of one another from hydrogen, C₁-C₆-alkyl,C₁-C₆-haloalkyl, halogen, cyano, NO₂, C₁-C₄-alkoxy, or C₁-C₄-haloalkoxy,or R⁸ is a phenyl ring or is a 3- to 6-membered unsaturated, partiallysaturated or saturated heterocycle, the heteroatoms being selected fromthe series N, S or O, and the phenyl ring or heterocycle beingoptionally substituted one or more times by identical or differentsubstituents, and the substituents being selectable independently of oneanother from hydrogen, C₁-C₆-alkyl, C₁-C₆-haloalkyl, halogen or cyano, Zis N, CH, CF, CCl, CBr or CI, R⁹, R¹⁰, R¹³, R¹⁴ and R¹⁵ independently ofone another are singly or multiply identically or differentlysubstituted C₁-C₆-alkyl or C₃-C₆-cycloalkyl, the substituents beingselectable independently of one another from halogen, cyano, a phenylring or a 3- to 6-membered unsaturated, partially saturated or saturatedheterocycle, the phenyl ring or heterocycle being optionally substitutedone or more times by identical or different substituents, and thesubstituents being selectable independently of one another fromhydrogen, C₁-C₆-alkyl, C₁-C₆-haloalkyl, halogen, cyano, NO₂,C₁-C₄-alkoxy, or C₁-C₄-haloalkoxy, or R⁹, R¹⁰, R¹³, R¹⁴, R¹⁵independently of one another are a phenyl ring or are a 3- to 6-memberedunsaturated, partially saturated or saturated heterocycle, theheteroatoms being selected from the series N, S and O, the phenyl ringor the heterocycle being optionally substituted one or more times byidentical or different substituents, and the substituents beingselectable independently of one another from hydrogen, C₁-C₆-alkyl,C₁-C₆-haloalkyl, halogen or cyano, R¹¹ and R¹² independently of oneanother are hydrogen or are R⁹, R¹⁶ is a phenyl ring or is a 5- or6-membered heteroaromatic ring where the heteroatoms are selected fromthe series N, S or O, the ring being optionally substituted one or moretimes by identical or different substituents, and the substituents beingselectable independently of one another from hydrogen, C₁-C₆-alkyl,C₁-C₆-haloalkyl, halogen, cyano, NO₂, C₁-C₄-alkoxy, or C₁-C₄-haloalkoxy,R¹⁷ is linear or branched —(C₁-C₄-alkylene)- or is a direct bond, Q_(Y)is a 5- or 6-membered, partially saturated or a saturated heterocyclicor heteroaromatic ring or an aromatic 8-, 9- or 10-membered fusedheterobicyclic ring system, the heteroatoms being selectable from theseries N, S or O, the ring or the ring system being optionallysubstituted one or more times by identical or different substituents,and the substituents being selectable independently of one another fromhydrogen, C₁-C₆-alkyl, C₂-C₆-alkenyl, C₂-C₆-alkynyl, C₃-C₆-cycloalkyl,C₁-C₆-haloalkyl, C₂-C₆-haloalkenyl, C₂-C₆-haloalkynyl,C₃-C₆-halocycloalkyl, halogen, CN, CO₂H, CO₂NH₂, NO₂, OH, C₁-C₄-alkoxy,C₁-C₄-haloalkoxy, C₁-C₄-alkylthio, C₁-C₄-alkylsulphinyl,C₁-C₄-alkylsulphonyl, C₁-C₄-haloalkylthio, C₁-C₄-halo-alkylsulphinyl, orC₁-C₄-haloalkylsulphonyl, or the substituents being selectableindependently of one another from phenyl or a 5- or 6-memberedheteroaromatic ring, where the phenyl or the ring may optionally besubstituted one or more times by identical or different C₁-C₆ alkylC₂-C₆-alkenyl, C₂-C₆-alkynyl, C₃-C₆-cycloalkyl, C₁-C₆-haloalkyl,C₂-C₆-haloalkenyl, C₂-C₆-haloalkynyl, C₃-C₆-halocycloalkyl, halogen, CN,NO₂, OH, C₁-C₄-alkoxy, or C₁-C₄-haloalkoxy substituents.
 3. Ananthranilic acid derivative of general formula (I) according to eitherof claim 1 or 2, in which R¹ is hydrogen, methyl, ethyl, cyclopropyl,cyanomethyl, methoxymethyl, methylthiomethyl, methylsulphinylmethyl, ormethylsulphonylmethyl, R² and R³ independently of one another arehydrogen, methyl, ethyl, isopropyl, or tert-butyl, R⁴ is —C(═O)—R⁸ or—C(═O)—OR⁹, R⁵ is hydrogen, C₁-C₄-alkyl, C₁-C₂-haloalkyl, halogen,cyano, or C₁-C₂-haloalkoxy, or two adjacent radicals R⁵ are —(CH₂)₄—,—(CH═CH—)₂—, —O(CH₂)₂O—, —O(CF₂)₂O—, —(CH═CH—CH═N)— or —(CH═CH—N═CH)—, nis 1 or 2, X is O, R⁶ is C₁-C₁-alkyl, C₃-C₆-cycloalkyl, C₁-C₄-haloalkyl,C₁-C₆-halocycloalkyl, C₂-C₆-alkenyl, C₂-C₄-haloalkenyl, C₂-C₄-alkynyl,C₂-C₄-haloalkynyl, C₁-C₄-alkoxy, C₁-C₄-haloalkoxy, fluoro, chloro,bromo, iodo, cyano, nitro, or C₃-C₆-trialkylsilyl, Q_(X) is a 5- or6-membered ring which is optionally substituted one or more times byidentical or different substituents R⁷ and is selected from the groupconsisting of furan, thiophene, pyrazole, triazole, imidazole, thiazole,oxazole, isoxazole, isothiazole, thiadiazole, oxadiazole, pyrrole,pyridine, pyrimidine, pyridazine and pyrazine, A is —CH₂—, —CH₂O—,—CH₂OCH₂—, —CH₂S—, —CH₂SCH₂—, —CH₂N(C₁-C₄-alkyl)-,—CH₂N(C₁-C₄-alkyl)CH₂—, —CH(Hal)-, —C(halo)₂-, —CH(CN)—, CH₂(CO)—,CH₂(CS)—, CH₂CH(OH)—, -cyclopropyl-, CH₂(CO)CH₂—, —CH(C₁-C₄-alkyl)-,—C(Di-C₁-C₆-alkyl)-, —CH₂CH₂—, —CH═CH—, —C≡C—, or —C═NO(C₁-C₆-alkyl), R⁷is methyl or is the radical

R independently at each occurrence is hydrogen, halogen, cyano, orC₁-C₄-haloalkyl, m is 1 or 2, Z is N, CH, CF, CCl or CBr, R⁸ ishydrogen, or is methyl, ethyl, isopropyl or tert-butyl optionally singlyor multiply identically or differently substituted, the substituentsbeing selectable independently of one another from halogen, cyano,phenyl or pyridyl, where the phenyl or pyridyl is optionally substitutedone or more times by identical or different hydrogen, trifluoromethyl,cyano, fluoro, chloro, bromo, or trifluoromethoxy substituents, or R⁸ isphenyl, or pyridyl or is a 3- to 6-membered saturated heterocycle,containing 1-2 heteroatoms from the series N, S or O, the phenyl orpyridyl ring or heterocycle being optionally substituted one or moretimes by identical or different substituents, and the substituents beingselectable independently of one another from hydrogen, C₁-C₆-alkyl,C₁-C₆-haloalkyl, halogen, or cyano, R⁹, R¹⁰, R¹³, R¹⁴ and R¹⁵independently of one another are optionally singly or multiplyidentically or differently substituted methyl, ethyl, isopropyl ortert-butyl, the substituents being selectable independently of oneanother from halogen, cyano, phenyl or pyridyl, where phenyl or pyridylis optionally substituted by one or more identical or differenttrifluoromethyl, cyano, fluoro, chloro, or trifluoromethoxysubstituents, or R⁹, R¹⁰, R¹³, R¹⁴ and R¹⁵ independently of one anotherare phenyl, pyridyl or are a 3- to 6-membered saturated heterocyclecontaining 1-2 heteroatoms from the series N, S or O, the phenyl orpyridinyl ring or the heterocycle being optionally substituted one ormore times by identical or different substituents, and the substituentsbeing selectable independently of one another from hydrogen,C₁-C₆-alkyl, C₁-C₆-haloalkyl, halogen, or cyano, R¹¹ and R¹²independently of one another are hydrogen or are R⁹, R¹⁶ is phenyl,pyridyl, pyrimidinyl, furan, or thiophene which is optionallysubstituted by one or chore identical or different substituents, thesubstituents being selectable independently of one another fromhydrogen, trifluoromethyl, cyano, fluoro, chloro, or trifluoromethoxy,R¹⁷ is methylene, ethylene, propylene, isopropylene, n-butylene,sec-butylene, isobutylene, or a direct bond, Q_(Y) is an optionallysingly or multiply identically or differently substituted 5- or6-membered heteroaromatic ring from the series Q-1 to Q-53, Q-58 toQ-59, Q-62 to Q-63, or an aromatic 9-membered fused heterobicyclic ringsystem Q-54 to Q-56, or a 5-membered heterocyclic ring Q-60 to Q-61, thesubstituents being selectable independently of one another fromC₁-C₄-alkyl, C₁-C₃-haloalkyl, C₁-C₂-alkoxy, halogen, cyano, hydroxyl,nitro, or C₁-C₂-haloalkoxy, or the substituents being selectableindependently of one another from phenyl or a 5- or 6-memberedheteroaromatic ring, where the phenyl or the ring may optionally besubstituted one or more times by identical or different C₁-C₆-alkyl,C₂-C₆-alkenyl, C₂-C₆-alkynyl, C₃-C₆-cycloalkyl, C₁-C₆-haloalkyl,C₂-C₆-haloalkenyl, C₂-C₆-haloalkynyl, C₃-C₆-halocycloalkyl, halogen, CN,NO₂, OH, C₁-C₄-alkoxy, or C₁-C₄-haloalkoxy substituents


4. A process for preparing a compound of the general formula (I)according to claim 1, comprising (A) reacting an aniline of formula (II)

in which R¹, R², R³, R⁴, R⁵, R⁶, X and n are as defined in claim 1, witha carbonyl chloride of the formula (III)

where Qx, A and Qy are as defined in claim 1, in the presence of anacid-binding agent; or (B) reacting an aniline of formula (II)

in which R¹, R², R³, R⁴, R⁵, R⁶, X and n are as defined in claim 1, witha carboxylic acid of formula (IV)

where Qx, A and Qy are as defined in claim 1, in the presence of acondensing agent; or (C) reacting a benzoxazinone of formula (V)

in which R⁵, R⁶, Qx, A, Qy and n are as defined in claim 1, with ahydrazine of formula (VI)

in which R², R³ and R⁴ are as defined in claim 1, in the presence of adiluent to form an anthranilamide compound of the formula (I) in whichR¹ is hydrogen; or (D) reacting an anthranilic hydrazide of formula(VII)

in which R¹, R²R³, R⁵, R⁶, X, n, Qx, A and Qy are as defined in claim 1,with a unit Y—R⁴, where R⁴ is as defined above and Y represents asuitable leaving group halogen or alkoxy; or (E) reacting an anthranilichydrazide of formula (VII)

in which R¹, R², R³, R⁵, R⁶, X, n, Qx, A and Qy are as defined in claim1, with an acid anhydride of the general formula (C(═O)—R⁸)₂O or(C(═O)—OR⁹)₂O or with an isocyanate of the formula O═C═NR¹¹R¹², whereR⁸, R⁹, R¹¹ and R¹² have the general definitions indicated in claim 1,to give compounds of the formula (I) of the invention.
 5. A mixturecomprising one or more compounds of the general formula (I) according toclaim 3, in which Qy is Q62 or Q63, and wherein the ratio of a compoundof the formula (I) in which Qy is Q62 to a compound of the formula (I)in which Qy is Q63 being 60:40 to 99:1.
 6. A mixture comprising one ormore compounds of the general formula (I) according to claim 3, in whichQy is Q58 or Q59, and wherein the ratio of a compound of the formula (I)in which Qy is Q58 to a compound of the formula (I) in which Qy is Q59being 60:40 to 99:1.
 7. A compound of general formula (VII),

in which R¹, R², R³, R⁵, R⁶, X, n, Qx, A and Qy are as defined inclaim
 1. 8. An agrochemical composition comprising at least one compoundof formula (I) according to claim 1 or the mixture of compounds offormula (I) according to claim 5 or claim 6, and one or more extendersand/or one or more surface-active substances.
 9. A process for producingan agrochemical composition comprising mixing at least one compound ofthe general formula (I) according to claim 1 or mixing the mixture ofcompounds of the general formula (I) according to claim 5 or claim 6with one or more extenders and/or one or more surface-active substances.10. (canceled)
 11. A method for controlling animal pests comprisingapplying a compound of the general formula (I) according to claim 1, orthe mixture of compounds of the general formula (I) according to claim 5or 6 to animal pests and/or phytopathogenic fungi and/or their habitatand/or seed.